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

HRID 1178595
Notes
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Reaction equation

HRID 1178595 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 9952828N-[4-[2-Amino-4-(3,5-dimethylphenyl)-1,3-thiazol-5-YL]-2-pyridyl]benzamide

Product 1

HCID 9911213N-[5-(2-BENZOYLAMINO-4-PYRIDYL)-4-(3,5-DIMETHYLPHENYL)-1,3-THIAZOL-2-YL]ACETAMIDEYield 30.1%

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 31374DimethylacetamideSolvent

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

  1. temperatureAfter the reaction mixture was cooled to room temperature
  2. filtrationThe resulting crude crystals were collected by filtration
  3. washwashed with water
  4. customThe crude crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-456e231578e040c39393f24f036b1189
Source dataset
uspto-grants-2007_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07276527B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes