Water → 4-[((1R)-1-{3-[(3-fluoro-4-methoxybenzoyl)amino]phenyl}ethyl)amino]quinazoline-8-carboxamide

HRID 474441

Reaction equation

HRID 474441 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C@H:8]([NH:10][C:11]2[C:20]3[C:15](=[C:16]([C:21]([NH2:23])=[O:22])[CH:17]=[CH:18][CH:19]=3)[N:14]=[CH:13][N:12]=2)[CH3:9])[CH:5]=[CH:6][CH:7]=1.[F:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[C:28](Cl)=[O:29].O>N1C=CC=CC=1>[F:24][C:25]1[CH:26]=[C:27]([CH:31]=[CH:32][C:33]=1[O:34][CH3:35])[C:28]([NH:1][C:2]1[CH:3]=[C:4]([C@H:8]([NH:10][C:11]2[C:20]3[C:15](=[C:16]([C:21]([NH2:23])=[O:22])[CH:17]=[CH:18][CH:19]=3)[N:14]=[CH:13][N:12]=2)[CH3:9])[CH:5]=[CH:6][CH:7]=1)=[O:29]

Participants

5

Reactant 3

HCID 962WaterHCID 27792553-Fluoro-4-methoxybenzoyl chlorideHCID 667628924-{[(1R)-1-(3-aminophenyl)ethyl]amino}quinazoline-8-carboxamide

Product 1

HCID 667623114-[((1R)-1-{3-[(3-fluoro-4-methoxybenzoyl)amino]phenyl}ethyl)amino]quinazoline-8-carboxamideYield 98%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A suspension of 4-{[(1R)-1-(3-aminophenyl)ethyl]amino}quinazoline-8-carboxamide (2.0 g, 6.51 mmol) in dry pyridine (50 mL) was treated with 3-fluoro-4-methoxybenzoyl chloride (1.51 g, 8.01 mmol, 1.23 eq), and the contents were stirred at room temp for 45 min. The clear-yellow solution was slowly added to water (1000 mL), and the white precipitate was filtered, washed with water (300 mL) and dried under vacuum at 35° C. to get the title compound in 98% yield (2.93 g).

Workup

  1. filtrationthe white precipitate was filtered
  2. washwashed with water (300 mL)
  3. customdried under vacuum at 35° C.

Sources & evidence

ORD record
ord-92f88f09e23b483db9ea94bf56d9b571
Source dataset
uspto-grants-2014_01
Patent number
US08637532B2

Linked notes

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