Sodium Hydroxide → 3-(1-cyanocyclopropyl)-N-[3-({2-[(hydroxyacetyl)amino]-1,3-benzothiazol-6-yl}oxy)-4-methylphenyl]benzamide

HRID 2190447Notes

Reaction equation

HRID 2190447 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:19][C:20](=[O:32])[C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]5([C:30]#[N:31])[CH2:29][CH2:28]5)[CH:22]=4)[CH:15]=[CH:16][C:17]=3[CH3:18])[CH:8]=[CH:7][C:5]=2[N:6]=1.C([O:36][CH2:37][C:38](Cl)=[O:39])(=O)C.[OH-].[Na+]>>[C:30]([C:27]1([C:23]2[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=2)[C:20]([NH:19][C:14]2[CH:15]=[CH:16][C:17]([CH3:18])=[C:12]([O:11][C:9]3[CH:8]=[CH:7][C:5]4[N:6]=[C:2]([NH:1][C:37](=[O:36])[CH2:38][OH:39])[S:3][C:4]=4[CH:10]=3)[CH:13]=2)=[O:32])[CH2:29][CH2:28]1)#[N:31]

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 26297Acetoxyacetyl chlorideHCID 86655387N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]-4-methylphenyl}-3-(1-cyanocyclopropyl)benzamide

Product 1

HCID 866553893-(1-cyanocyclopropyl)-N-[3-({2-[(hydroxyacetyl)amino]-1,3-benzothiazol-6-yl}oxy)-4-methylphenyl]benzamideYield 14%

Procedure

Using N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]-4-methylphenyl}-3-(1-cyanocyclopropyl)benzamide (0.11 g, 0.25 mmol) produced in Example A35(iv), 2-chloro-2-oxoethyl acetate (0.27 g, 2.0 mmol), and 8N aqueous sodium hydroxide solution (1 mL), and in the same manner as in Example A30, the title compound (17 mg, 14%) was obtained as a pale-yellow powder.

Sources & evidence

ORD record
ord-3b453f6d784344b7b2fcdef2c6d65d6e
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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