Methanesulfonyl chloride → (2R,5R)-5-Chloromethyl-4-{2-[6-(difluoro-phenyl-methyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-c]pyridin-1-yl]-2-oxo-ethyl}-2-methyl-piperazine-1-carboxylic acid tert-butyl ester

HRID 1475480Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([CH2:14]O)[N:11]([CH2:16][C:17]([N:19]2[C:27]3[CH:26]=[C:25]([C:28]([F:36])([F:35])[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[N:24]=[CH:23][C:22]=3[C:21]([CH3:38])([CH3:37])[CH2:20]2)=[O:18])[CH2:10][C@H:9]1[CH3:39])=[O:7])([CH3:4])([CH3:3])[CH3:2].CS([Cl:44])(=O)=O>>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([CH2:14][Cl:44])[N:11]([CH2:16][C:17]([N:19]2[C:27]3[CH:26]=[C:25]([C:28]([F:36])([F:35])[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[N:24]=[CH:23][C:22]=3[C:21]([CH3:38])([CH3:37])[CH2:20]2)=[O:18])[CH2:10][C@H:9]1[CH3:39])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 31297Methanesulfonyl chloride

HCID 70981318(2R,5R)-4-{2-[6-(Difluoro-phenyl-methyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-c]pyridin-1-yl]-2-oxo-ethyl}-5-hydroxymethyl-2-methyl-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86724029(2R,5R)-5-Chloromethyl-4-{2-[6-(difluoro-phenyl-methyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-c]pyridin-1-yl]-2-oxo-ethyl}-2-methyl-piperazine-1-carboxylic acid tert-butyl esterYield 71%

Procedure

The title compound was prepared following methods similar to those described in Preparation 351 starting from (2R,5R)-4-{2-[6-(difluoro-phenyl-methyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-c]pyridin-1-yl]-2-oxo-ethyl}-5-hydroxymethyl-2-methyl-piperazine-1-carboxylic acid tert-butyl ester (1.37 g, 2.5 mmol), methanesulfonyl chloride (234 μL, 3.0 mmol) and TEA (582 μL, 4.0 mmol) to give the title compound (1.0 g) as a pale yellow gum. MS: [M+H]+=563.

Workup

customThe title compound was prepared

Sources & evidence

ORD record: ord-8f5736ffbf25456da376ac2612ad48e9
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018214B2

Reaction notes

Loading…