Ammonia → HCID 86686096, compound

HRID 1469003Notes

Reaction equation

HRID 1469003 reaction equation
CO.[NH3:3].Cl[C:5]1[C:14]2[C:9](=[CH:10][C:11]([F:24])=[C:12]([O:15][C:16]3[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:17]=3[CH3:23])[CH:13]=2)[N:8]=[C:7]([N:25]2[CH:29]=[C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:27]=[N:26]2)[N:6]=1>C1COCC1>[NH2:3][C:5]1[C:14]2[C:9](=[CH:10][C:11]([F:24])=[C:12]([O:15][C:16]3[C:21]([CH3:22])=[CH:20][CH:19]=[CH:18][C:17]=3[CH3:23])[CH:13]=2)[N:8]=[C:7]([N:25]2[CH:29]=[C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:27]=[N:26]2)[N:6]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 86686095HCID 86686095, compound

Product 1

HCID 86686096HCID 86686096, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A methanol solution of ammonia (7M, 0.39 mL, 2.7 mmol) was added to a solution of the above 1-[4-chloro-6-(2,6-dimethyl-phenoxy)-7-fluoro-quinazolin-2-yl]-1H-pyrazole-4-carboxylic acid, ethyl ester (120 mg, 0.27 mmol) and THF (2 mL). The mixture was stirred 6 h, then concentrated. The residue was triturated with Et2O, providing the titled compound (72 mg, 64%). 1H NMR (500 MHz, DMSO-d6): 8.96 (d, J=0.8 Hz, 1H), 8.44-8.02 (m, 3H), 7.71 (d, J=11.9 Hz, 1H), 7.37 (d, J=9.0 Hz, 1H), 7.24-7.20 (m, 2H), 7.17 (dd, J=8.6, 6.2 Hz, 1H), 4.27 (q, J=7.1 Hz, 2H), 2.12 (s, 6H), 1.31 (t, J=7.1 Hz, 3H).

Workup

  1. concentrationconcentrated
  2. customThe residue was triturated with Et2O

Sources & evidence

ORD record
ord-9fafe6c53bcd4c76bf54bf848bf8a25c
Source dataset
uspto-grants-2015_04
Patent number
US09006251B2

Reaction notes

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