4-Fluorobenzoyl chloride → HCID 86703383, compound

HRID 512548Notes

Reaction equation

HRID 512548 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[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=[CH:20][CH:19]=2)=[N:14][C:13]=1[C:28]([NH2:30])=[O:29]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[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[C:27]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[N:21]=[CH:20][CH:19]=3)=[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 867033825-Amino-2-(quinolin-4-ylamino)thiazole-4-carboxamide

Product 1

HCID 86703383HCID 86703383, compoundYield 33.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent2×

Procedure

To a mixture of 4-fluorobenzoylchloride (0.16 g, 1 mmol) and a catalytic amount of DMAP in pyridine (5 mL) was added dropwise a solution of 5-amino-2-(quinolin-4-ylamino)thiazole-4-carboxamide (0.25 g, 0.87 mmol) in pyridine (5 mL), and the mixture was stirred for 16 hrs at rt. The reaction mixture was quenched with ice-water. The resulting solids were collected by filteration and washed successively with water, ether, and MeOH to give 0.12 g (33% yield) of the titled compound. LCMS m/z [M+H]+408.2 .

Workup

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

Sources & evidence

ORD record
ord-640872fda575459c98ad1694d188d28b
Source dataset
uspto-grants-2015_08
Patent number
US09102637B2

Reaction notes

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