6-(cyclopropanecarbonylamino)-4-[3-(5-fluoropyrimidin-2-yl)-2-methoxy-anilino]-N-(trideuteriomethyl)pyridine-3-carboxamide

ID: ALA4789639

Cas Number: 1771691-34-9

PubChem CID: 155981972

Product Number: B649357, Order Now?

Max Phase: Phase

Molecular Formula: C22H21FN6O3

Molecular Weight: 436.45

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Bms-986202 | BMS986202

Canonical SMILES:  [2H]C([2H])([2H])NC(=O)c1cnc(NC(=O)C2CC2)cc1Nc1cccc(-c2ncc(F)cn2)c1OC

Standard InChI:  InChI=1S/C22H21FN6O3/c1-24-22(31)15-11-25-18(29-21(30)12-6-7-12)8-17(15)28-16-5-3-4-14(19(16)32-2)20-26-9-13(23)10-27-20/h3-5,8-12H,6-7H2,1-2H3,(H,24,31)(H2,25,28,29,30)/i1D3

Standard InChI Key:  BBRMAVGRWHNAIG-FIBGUPNXSA-N

Molfile:  

155981972
     RDKit          2D

 35 38  0  0  0  0  0  0  0  0999 V2000
   33.0175   -7.4105    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   24.9114  -12.0907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2623   -6.6305    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.8582   -5.0705    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.2623   -9.7505    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5602   -9.7505    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.5602   -5.0705    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.5072   -7.4105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   30.3154   -4.2905    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   28.9644   -6.6305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.6133  -12.0907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.3933  -13.4415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.1733  -12.0907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2623  -11.3107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9114   -8.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9114   -7.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.5602   -6.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2093   -7.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2093   -8.9705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9114   -4.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2623   -5.0705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8582   -6.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6133   -4.2905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.9114   -2.7305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6133   -2.7305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2623   -1.9505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.9644   -5.0705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1561   -6.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.6133   -7.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6665   -5.0705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.3154   -7.4105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6665   -6.6305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3185   -6.1470    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   17.6724   -7.4681    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   18.6396   -5.7928    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 32  1  0
  2 14  2  0
  3 21  1  0
  3 29  1  0
  4 22  2  0
  5 14  1  0
  5 15  1  0
  6 15  2  0
  6 19  1  0
  7 17  1  0
  7 20  1  0
  8 22  1  0
  8 28  1  0
  9 27  2  0
  9 30  1  0
 10 27  1  0
 10 31  2  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 12 13  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 22  1  0
 20 21  1  0
 20 24  2  0
 21 23  2  0
 23 25  1  0
 23 27  1  0
 24 26  1  0
 25 26  2  0
 28 33  1  0
 28 34  1  0
 28 35  1  0
 30 32  2  0
 31 32  1  0
M  ISO  3  33   2  34   2  35   2
M  END

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: Yes

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 436.45

Molecular Weight (Monoisotopic): 436.1659

AlogP: 3.14

#Rotatable Bonds: 7

Polar Surface Area: 118.13

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 11.84

CX Basic pKa: 6.59

CX LogP: 3.40

CX LogD: 3.39

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.52

Np Likeness Score: -1.30

References

1. Liu C,Lin J,Langevine C,Smith D,Li J,Tokarski JS,Khan J,Ruzanov M,Strnad J,Zupa-Fernandez A,Cheng L,Gillooly KM,Shuster D,Zhang Y,Thankappan A,McIntyre KW,Chaudhry C,Elzinga PA,Chiney M,Chimalakonda A,Lombardo LJ,Macor JE,Carter PH,Burke JR,Weinstein DS.  (2021)  Discovery of BMS-986202: A Clinical Tyk2 Inhibitor that Binds to Tyk2 JH2.,  64  (1.0): [PMID:33370104] [10.1021/acs.jmedchem.0c01698]

2. Unpublished dataset, 

Source

Source(2):

• Scientific Literature
• Clinical Candidates