2-Bromo-1-(2,4-dimethyl-1,3-thiazol-5-yl)ethan-1-one → N-[2-(4-Carbomethoxymethoxyphenyl)-1-methylethyl]-2-hydroxy-2-(2,4-dimethyl-thiazol-5-yl)ethanamine

HRID 1587920Notes

Reaction equation

HRID 1587920 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:8](=[O:11])[CH2:9]Br)=[C:5]([CH3:7])[N:6]=1.[C:12]([CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([NH2:27])[CH3:26])=[CH:20][CH:19]=1)([O:14][CH3:15])=[O:13]>>[C:12]([CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH:25]([NH:27][CH2:9][CH:8]([OH:11])[C:4]2[S:3][C:2]([CH3:1])=[N:6][C:5]=2[CH3:7])[CH3:26])=[CH:20][CH:19]=1)([O:14][CH3:15])=[O:13]

Participants

3

Reactant 2

HCID 126684222-Bromo-1-(2,4-dimethyl-1,3-thiazol-5-yl)ethan-1-oneHCID 14372867Methyl 2-[4-(2-aminopropyl)phenoxy]acetate

Product 1

HCID 19974107N-[2-(4-Carbomethoxymethoxyphenyl)-1-methylethyl]-2-hydroxy-2-(2,4-dimethyl-thiazol-5-yl)ethanamine

Procedure

Prepared analogously to Example 3 by reaction of 2,4-dimethyl-5-bromoacetyl-thiazole with 2-(4-carbomethoxymethoxyphenyl)-1-methylethylamine, followed by reduction and purification of the base on a silica gel column using ethyl acetate/methanol=17:3.

Workup

  1. customfollowed by reduction and purification of the base on a silica gel column

Sources & evidence

ORD record
ord-e459b9c8cbd8478fa5a0a84e0086fbd0
Source dataset
uspto-grants-1993_06
Patent number
US05219852

Reaction notes

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