Benzoyl chloride → N-[4-[2-Benzoylamino-4-(4-methoxyphenyl)-1,3-thiazol-5-YL]-2-pyridyl]benzamide

HRID 1178588Notes

Reaction equation

[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]1[S:12][C:13]([C:24]2[CH:29]=[CH:28][N:27]=[C:26]([NH2:30])[CH:25]=2)=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[N:15]=1.[C:31](=[O:34])([O-])O.[Na+]>CN(C)C1C=CN=CC=1.CN(C)C(=O)C>[C:1]([NH:10][C:11]1[S:12][C:13]([C:24]2[CH:29]=[CH:28][N:27]=[C:26]([NH:30][C:31](=[O:34])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:25]=2)=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2)[N:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Benzoyl chloride (0.59 g, 4.2 mmol) and 4-dimethylaminopyridine (0.05 g, 0.4 mmol) were added to a solution of 4-[2-amino-4-(4-methoxyphenyl)-1,3-thiazol-5-yl]-2-pyridylamine (0.42 g, 1.4 mmol) in N,N-dimethylacetamide (10 mL) and the mixture was stirred at 70° C. for 19 hours. After the reaction mixture was cooled to room temperature, a saturated aqueous solution of sodium hydrogencarbonate (50 mL) was added. The resulting crude crystals were collected by filtration and washed with water. The crude crystals were recrystallized from ethanol to obtain 0.26 g (0.51 mmol, yield 37%) of the title compound.

Workup

temperatureAfter the reaction mixture was cooled to room temperature
filtrationThe resulting crude crystals were collected by filtration
washwashed with water
customThe crude crystals were recrystallized from ethanol

Sources & evidence

ORD record: ord-c10c6cc00649413ab9dfabbbddcfa6f4
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07276527B2

Reaction notes

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