Acetoxyacetyl chloride → 3-(1-cyano-1-methylethyl)-N-(3-{[2-(glycoloylamino)-1,3-benzothiazol-6-yl]oxy}-4-methoxyphenyl)benzamide

HRID 2190414Notes

Reaction equation

HRID 2190414 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]3[CH:13]=[C:14]([NH:20][C:21](=[O:33])[C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([C:31]#[N:32])([CH3:30])[CH3:29])[CH:23]=4)[CH:15]=[CH:16][C:17]=3[O:18][CH3:19])[CH:8]=[CH:7][C:5]=2[N:6]=1.C([O:37][CH2:38][C:39](Cl)=[O:40])(=O)C>CN(C)C=O>[C:31]([C:28]([C:24]1[CH:23]=[C:22]([CH:27]=[CH:26][CH:25]=1)[C:21]([NH:20][C:14]1[CH:15]=[CH:16][C:17]([O:18][CH3:19])=[C:12]([O:11][C:9]2[CH:8]=[CH:7][C:5]3[N:6]=[C:2]([NH:1][C:38](=[O:37])[CH2:39][OH:40])[S:3][C:4]=3[CH:10]=2)[CH:13]=1)=[O:33])([CH3:30])[CH3:29])#[N:32]

Participants

4

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 86655369HCID 86655369, compound

Product 1

HCID 866553713-(1-cyano-1-methylethyl)-N-(3-{[2-(glycoloylamino)-1,3-benzothiazol-6-yl]oxy}-4-methoxyphenyl)benzamideYield 49%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Using N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]-4-methoxyphenyl}-3-(1-cyano-1-methylethyl)benzamide (230 mg, 0.50 mmol) produced in Example A21(iv), 2-chloro-2-oxoethyl acetate (273 mg, 2.00 mmol) and N,N-dimethylformamide (5 mL), and in the same manner as in Example A19, the title compound (126 mg, 49%) was obtained as a pale-yellow powder.

Sources & evidence

ORD record
ord-45a72658159b47c5bfbb015bdc3deaf3
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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