Acetyl chloride → N-[5-(2-BENZOYLAMINO-4-PYRIDYL)-4-(3,5-DIMETHYLPHENYL)-1,3-THIAZOL-2-YL]ACETAMIDE

HRID 2212352Notes

Reaction equation

[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[S:7][C:8]([C:19]2[CH:24]=[CH:23][N:22]=[C:21]([NH:25][C:26](=[O:33])[C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH:20]=2)=[C:9]([C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[CH:12]=2)[N:10]=1.C(=O)([O-])O.[Na+]>CN(C)C1C=CN=CC=1.CN(C)C(=O)C>[C:26]([NH:25][C:21]1[CH:20]=[C:19]([C:8]2[S:7][C:6]([NH:5][C:1](=[O:3])[CH3:2])=[N:10][C:9]=2[C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[C:13]([CH3:18])[CH:12]=2)[CH:24]=[CH:23][N:22]=1)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 70 °C

Procedure

Acetyl chloride (0.26 mL, 3.7 mmol) and 4-dimethylaminopyridine (0.09 g, 0.76 mmol) were added to a solution of N-[4-[2-amino-4-(3,5-dimethylphenyl)-1,3-thiazol-5-yl]-2-pyridyl]benzamide (0.96 g, 2.4 mmol) in N,N-dimethylacetamide (20 mL) and the mixture was stirred at 70° C. for 16 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 ethyl acetate to obtain 0.32 g (yield 30%) 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 ethyl acetate

Sources & evidence

ORD record: ord-d7aec1ab3c48415785ec569a6081e1ac
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07101899B1

Reaction notes

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