N2-(3-chloro-4-morpholinophenyl)-N4-(2,2,2-trifluoroethyl)furo[3,2-d]pyrimidine-2,4-diamine

ID: ALA4078893

PubChem CID: 68755406

Max Phase: Preclinical

Molecular Formula: C18H17ClF3N5O2

Molecular Weight: 427.81

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  FC(F)(F)CNc1nc(Nc2ccc(N3CCOCC3)c(Cl)c2)nc2ccoc12

Standard InChI:  InChI=1S/C18H17ClF3N5O2/c19-12-9-11(1-2-14(12)27-4-7-28-8-5-27)24-17-25-13-3-6-29-15(13)16(26-17)23-10-18(20,21)22/h1-3,6,9H,4-5,7-8,10H2,(H2,23,24,25,26)

Standard InChI Key:  WHFIWINTCCNYQZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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    4.5232  -22.0627    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2328  -21.6533    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2300  -20.8306    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5214  -20.4254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5207  -19.6082    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2281  -19.1990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2274  -18.3818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9348  -17.9726    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.5194  -17.9738    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.2209  -17.5614    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.9412  -22.0608    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6482  -21.6511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3533  -22.0590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0598  -21.6499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0590  -20.8319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3457  -20.4246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6420  -20.8359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8126  -21.6510    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8118  -20.8327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0333  -20.5806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5529  -21.2431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0347  -21.9046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7600  -20.4224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.4688  -20.8311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1732  -20.4239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1750  -19.6064    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4663  -19.1977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7557  -19.6065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7680  -22.0578    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
 18  1  1  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4 19  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
  2 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 22 18  1  0
 23 24  1  0
 23 28  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  0
 15 23  1  0
 14 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4078893

   2-N-(3-chloro-4-morpholin-4-ylphenyl)-4-N-(2,2,2-trifluoroethyl)furo[3,2-d]pyrimidine-2,4-diamine

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: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 427.81

Molecular Weight (Monoisotopic): 427.1023

AlogP: 4.43

#Rotatable Bonds: 5

Polar Surface Area: 75.45

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 12.62

CX Basic pKa: 4.10

CX LogP: 4.23

CX LogD: 4.23

Aromatic Rings: 3

Heavy Atoms: 29

QED Weighted: 0.62

Np Likeness Score: -1.76

References

1. Hoemann M, Wilson N, Argiriadi M, Banach D, Burchat A, Calderwood D, Clapham B, Cox P, Duignan DB, Konopacki D, Somal G, Vasudevan A..  (2016)  Synthesis and optimization of furano[3,2-d]pyrimidines as selective spleen tyrosine kinase (Syk) inhibitors.,  26  (22): [PMID:27789138] [10.1016/j.bmcl.2016.09.077]

Source

Source(1):

• Scientific Literature