(Bis(2-methoxyethyl)amino)sulfur trifluoride → N-[(1RS,2SR)-2-(3-Fluoro-pyrrolidin-1-yl)-cyclopentyl]-2-methoxy-6-methylsulfanyl-4-trifluoromethyl-benzamide

HRID 1950974Notes

Reaction equation

HRID 1950974 reaction equation
O[CH:2]1[CH2:6][CH2:5][N:4]([CH:7]2[CH2:11][CH2:10][CH2:9][CH:8]2[NH:12][C:13](=[O:28])[C:14]2[C:19]([S:20][CH3:21])=[CH:18][C:17]([C:22]([F:25])([F:24])[F:23])=[CH:16][C:15]=2[O:26][CH3:27])[CH2:3]1.COCCN(S(F)(F)[F:39])CCOC>>[F:39][CH:2]1[CH2:6][CH2:5][N:4]([CH:7]2[CH2:11][CH2:10][CH2:9][CH:8]2[NH:12][C:13](=[O:28])[C:14]2[C:19]([S:20][CH3:21])=[CH:18][C:17]([C:22]([F:25])([F:24])[F:23])=[CH:16][C:15]=2[O:26][CH3:27])[CH2:3]1

Participants

3

Reactant 2

HCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 66682712N-[(1RS,2SR)-2-(3-Hydroxy-pyrrolidin-1-yl)-cyclopentyl]-2-methoxy-6-methylsulfanyl-4-trifluoromethyl-benzamide

Product 1

HCID 66681406N-[(1RS,2SR)-2-(3-Fluoro-pyrrolidin-1-yl)-cyclopentyl]-2-methoxy-6-methylsulfanyl-4-trifluoromethyl-benzamide

Procedure

The title compound, light yellow solid, MS: m/e=421.1 [(M+H)+], was prepared in accordance with the general method of example 17 from N-[(1RS,2SR)-2-(3-hydroxy-pyrrolidin-1-yl)-cyclopentyl]-2-methoxy-6-methylsulfanyl-4-trifluoromethyl-benzamide (example 63) and bis(2-methoxyethyl)aminosulfur trifluoride. The two diastereomers were not separated.

Sources & evidence

ORD record
ord-921322b4f2c4498b9d475ff7e3a1b59e
Source dataset
uspto-grants-2013_03
Patent number
US08404673B2

Reaction notes

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