Methanol → 3-(2-(4-fluorobenzoyl)quinazolin-4-ylamino)-1H-pyrazole-5-carbonitrile

HRID 625743Notes

Reaction equation

HRID 625743 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([C:12]([C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)=[O:13])[N:3]=1.[NH2:21][C:22]1[CH:26]=[C:25]([C:27]#[N:28])[NH:24][N:23]=1.CO>CN(C=O)C>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:12]([C:4]2[N:3]=[C:2]([NH:21][C:22]3[CH:26]=[C:25]([C:27]#[N:28])[NH:24][N:23]=3)[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=2)=[O:13])=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 211805745-Amino-1H-pyrazole-3-carbonitrileHCID 86649048(4-Chloroquinazolin-2-yl)(4-fluorophenyl)methanone

Product 1

HCID 568485463-(2-(4-fluorobenzoyl)quinazolin-4-ylamino)-1H-pyrazole-5-carbonitrileYield 23.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of (4-chloroquinazoline-2-yl)(4-fluorophenyl)methanone from Example 3 (580 mg, 2.02 mmol), and 3-amino-1H-pyrazole-5-carbonitrile (218 mg, 2.02 mmol) in DMF (5 mL) was stirred at rt overnight. MeOH (10 mL) was then added to this mixture, and the precipitate was filtered washed with MeOH, and dried to afford 3-(2-(4-fluorobenzoyl)quinazolin-4-ylamino)-1H-pyrazole-5-carbonitrile (170 mg, 23.4%) 1H NMR (300 MHz, DMSO-d6) δ 6.89 (s, 1H), 7.40 (d, 2H), 7.83 (s, 1H), 7.98 (m, 2H), 8.11 (m, 2H), 8.56 (s, 1H), 11.18 (s, 1H), 13.84 (s, 1H); LC-MS (ESI) m/z 359 (M+H)+.

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with MeOH
  3. customdried

Sources & evidence

ORD record
ord-cbb08b6c34b540b68f2958c0c83cb07f
Source dataset
uspto-grants-2016_04
Patent number
US09308207B2

Reaction notes

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