Acetoxyacetyl chloride → 3-(1-cyanocyclopropyl)-N-(3-{[2-(glycoloylamino)-1,3-benzothiazol-6-yl]oxy}phenyl)benzamide

HRID 2190402Notes

Reaction equation

HRID 2190402 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:18][C:19](=[O:31])[C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]5([C:29]#[N:30])[CH2:28][CH2:27]5)[CH:21]=4)[CH:15]=[CH:16][CH:17]=3)[CH:8]=[CH:7][C:5]=2[N:6]=1.C([O:35][CH2:36][C:37](Cl)=[O:38])(=O)C>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:29]([C:26]1([C:22]2[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=2)[C:19]([NH:18][C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([O:11][C:9]3[CH:8]=[CH:7][C:5]4[N:6]=[C:2]([NH:1][C:36](=[O:35])[CH2:37][OH:38])[S:3][C:4]=4[CH:10]=3)[CH:13]=2)=[O:31])[CH2:27][CH2:28]1)#[N:30]

Participants

5

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 86655364N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]phenyl}-3-(1-cyanocyclopropyl)benzamide

Product 1

HCID 583490523-(1-cyanocyclopropyl)-N-(3-{[2-(glycoloylamino)-1,3-benzothiazol-6-yl]oxy}phenyl)benzamideYield 26.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Using N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]phenyl}-3-(1-cyanocyclopropyl)benzamide (310 mg, 726 μmol) produced in Example A15(iii), pyridine (10 mL), 2-chloro-2-oxoethyl acetate (269 mg, 1.97 mmol) and N,N-dimethylpyridine-4-amine (62.1 mg, 508 μmol) as starting materials, and in the same manner as in Example A14, the title compound (93 mg, 26%) was obtained as colorless crystals. In this Example, the purification operation was performed using silica gel column chromatography (hexane/ethyl acetate=5/95→20/80).

Sources & evidence

ORD record
ord-28f4d4a21db145b1bd07e1a02750e205
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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