Dimethyl Sulfoxide → N-[2-(4-Carbomethoxymethoxyphenyl)-1-methylethyl]-2-hydroxy-2-(2-trifluoromethyl-thiazol-4-yl)ethanamine

HRID 477159Notes

Reaction equation

HRID 477159 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[S:4][CH:5]=[C:6]([CH:8]2[O:10][CH2:9]2)[N:7]=1.[C:13]([CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH:26]([NH2:28])[CH3:27])=[CH:21][CH:20]=1)([O:15][CH3:16])=[O:14].CS(C)=O.CCOCC>C(Cl)Cl.CO>[C:13]([CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH:26]([NH:28][CH2:9][CH:8]([OH:10])[C:6]2[N:7]=[C:3]([C:2]([F:12])([F:11])[F:1])[S:4][CH:5]=2)[CH3:27])=[CH:21][CH:20]=1)([O:15][CH3:16])=[O:14]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 3283Diethyl EtherHCID 143728612-(2-Trifluoromethyl-thiazol-4-yl)ethylene oxideHCID 14372867Methyl 2-[4-(2-aminopropyl)phenoxy]acetate

Product 1

HCID 14347763N-[2-(4-Carbomethoxymethoxyphenyl)-1-methylethyl]-2-hydroxy-2-(2-trifluoromethyl-thiazol-4-yl)ethanamine

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared by analogy to Example 104 by reaction of 2-(2-trifluoromethyl-thiazol-4-yl)ethylene oxide with 2-(4-carbomethoxymethoxyphenyl)-1-methylethylamine and dimethyl sulfoxide at 90° C. for 16 hours. The base is obtained by extraction by shaking with ether and purification on a silica gel column using methylene chloride/methanol 20:1 as eluant.

Workup

  1. customThe base is obtained by extraction

Sources & evidence

ORD record
ord-0f7cc50781024ff78bed3bfeb308e48c
Source dataset
uspto-grants-1989_12
Patent number
US04886814

Reaction notes

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