Methyl 4-(3-Chloro-4-fluorophenyl)-4-methyl-6-(morpholinomethyl)-2-thiazol-2-yl-1H-pyrimidine-5-carboxylate

ID: ALA4555377

PubChem CID: 155556898

Max Phase: Preclinical

Molecular Formula: C21H22ClFN4O3S

Molecular Weight: 464.95

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COC(=O)C1=C(CN2CCOCC2)NC(c2nccs2)=NC1(C)c1ccc(F)c(Cl)c1

Standard InChI:  InChI=1S/C21H22ClFN4O3S/c1-21(13-3-4-15(23)14(22)11-13)17(20(28)29-2)16(12-27-6-8-30-9-7-27)25-18(26-21)19-24-5-10-31-19/h3-5,10-11H,6-9,12H2,1-2H3,(H,25,26)

Standard InChI Key:  YENLKMPVUICIFW-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    9.0745   -8.1211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5946   -8.7457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3041   -9.1502    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3041   -9.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5946  -10.3837    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.8892   -9.9713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8892   -9.1502    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1823   -8.7413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1823   -7.9264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4777   -9.1473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7708   -8.7383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1762  -10.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1762  -11.1907    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4698  -11.5965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4698  -12.4176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1734  -12.8329    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8841  -12.4194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8841  -11.5983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0094  -10.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7601  -10.0402    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   12.3062  -10.6470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8989  -11.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0993  -11.1899    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.1187   -8.1211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9256   -8.2657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4456   -7.6300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1629   -6.8607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3601   -6.7273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8359   -7.3519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6871   -6.2328    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.2523   -7.7673    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  4  3  2  0
  5  4  1  0
  6  5  1  0
  7  6  2  0
  2  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
  6 12  1  0
 12 13  1  0
 13 14  1  0
 15 14  1  0
 16 15  1  0
 17 16  1  0
 18 17  1  0
 13 18  1  0
  4 19  1  0
 19 20  1  0
 21 20  1  0
 22 21  2  0
 23 22  1  0
 19 23  2  0
  2 24  1  0
 24 25  2  0
 26 25  1  0
 27 26  2  0
 28 27  1  0
 29 28  2  0
 24 29  1  0
 27 30  1  0
 26 31  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4555377

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 464.95

Molecular Weight (Monoisotopic): 464.1085

AlogP: 2.96

#Rotatable Bonds: 5

Polar Surface Area: 76.05

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.65

CX LogP: 2.70

CX LogD: 2.70

Aromatic Rings: 2

Heavy Atoms: 31

QED Weighted: 0.69

Np Likeness Score: -1.47

References

1. Qiu Z, Lin X, Zhou M, Liu Y, Zhu W, Chen W, Zhang W, Guo L, Liu H, Wu G, Huang M, Jiang M, Xu Z, Zhou Z, Qin N, Ren S, Qiu H, Zhong S, Zhang Y, Zhang Y, Wu X, Shi L, Shen F, Mao Y, Zhou X, Yang W, Wu JZ, Yang G, Mayweg AV, Shen HC, Tang G..  (2016)  Design and Synthesis of Orally Bioavailable 4-Methyl Heteroaryldihydropyrimidine Based Hepatitis B Virus (HBV) Capsid Inhibitors.,  59  (16): [PMID:27458651] [10.1021/acs.jmedchem.6b00879]

Source

Source(1):

• Scientific Literature