Acetyl chloride → HCID 59507064, compound

HRID 1800597Notes

Reaction equation

HRID 1800597 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6]([O:11][C:12]1[CH:13]=[C:14]([NH:19][C:20](=[O:32])[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([C:30]#[N:31])([CH3:29])[CH3:28])[CH:22]=3)[CH:15]=[CH:16][C:17]=1[CH3:18])[N:5]=2.[C:33](Cl)(=[O:35])[CH3:34]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:33]([NH:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6]([O:11][C:12]1[CH:13]=[C:14]([NH:19][C:20](=[O:32])[C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([C:30]#[N:31])([CH3:29])[CH3:28])[CH:22]=3)[CH:15]=[CH:16][C:17]=1[CH3:18])[N:5]=2)(=[O:35])[CH3:34]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 86646043HCID 86646043, compound

Product 1

HCID 59507064HCID 59507064, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of N-{3-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-methylphenyl}-3-(1-cyano-1-methylethyl)benzamide (200 mg, 0.450 mmol) produced in Example C12(iv) in pyridine (5 mL) were added acetyl chloride (128 μL, 1.80 mmol) and N,N-dimethylpyridine-4-amine (8.8 mg, 0.0720 mmol), and the mixture was stirred at room temperature for 28 hr. The title compound (157 mg, 72%) was obtained as white crystals by operation in the same manner as in Example C81. The present compound was recrystallized from ethyl acetate and tetrahydrofuran.

Sources & evidence

ORD record
ord-bc9cbc96b9d247d6b09c2e3fccdcb0ee
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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