4-Fluorobenzoyl chloride → 5-(4-Fluorobenzamido)-2-(quinolin-6-ylamino)thiazole-4-carboxamide

HRID 512540

Reaction equation

HRID 512540 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[NH2:11][C:12]1[S:16][C:15]([NH:17][C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][CH:27]=2)[N:24]=[CH:23][CH:22]=[CH:21]3)=[N:14][C:13]=1[C:28]([NH2:30])=[O:29]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH:11][C:12]2[S:16][C:15]([NH:17][C:18]3[CH:19]=[C:20]4[C:25](=[CH:26][CH:27]=3)[N:24]=[CH:23][CH:22]=[CH:21]4)=[N:14][C:13]=2[C:28]([NH2:30])=[O:29])=[O:7])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 678794-Fluorobenzoyl chlorideHCID 867033765-Amino-2-(quinolin-6-ylamino)thiazole-4-carboxamide

Product 1

HCID 867033775-(4-Fluorobenzamido)-2-(quinolin-6-ylamino)thiazole-4-carboxamideYield 42.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent2×

Procedure

To solution of 4-fluorobenzoyl chloride (0.16 g, 1.2 mmol) in pyridine (5 mL) was added dropwise a solution of 5-amino-2-(quinolin-6-ylamino)thiazole-4-carboxamide (0.30 g, 1.05 mmol) and a catalytic amount of DMAP in pyridine (5 mL) at 0° C., and the mixture was stirred for 16 hrs at rt. The reaction mixture was quenched with ice-water. The resulting solids were collected by filtration and washed successively with water, MeOH and ether to give 0.18 g (42% yield) of the titled compound.

Workup

  1. customThe reaction mixture was quenched with ice-water
  2. filtrationThe resulting solids were collected by filtration
  3. washwashed successively with water, MeOH and ether

Sources & evidence

ORD record
ord-e7cccd176a5c43068be1214f64b9a466
Source dataset
uspto-grants-2015_08
Patent number
US09102637B2

Linked notes

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