(R)-3-Methylmorpholine → (2R,5S)-4-{2-[6-(1,1-Difluoro-butyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-2-oxo-ethyl}-2-methyl-5-((R)-3-methyl-morpholin-4-ylmethyl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1475516Notes

Reaction equation

HRID 1475516 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([CH2:14]Cl)[N:11]([CH2:16][C:17]([N:19]2[C:27]3[C:22](=[N:23][CH:24]=[C:25]([C:28]([F:33])([F:32])[CH2:29][CH2:30][CH3:31])[CH:26]=3)[C:21]([CH3:35])([CH3:34])[CH2:20]2)=[O:18])[CH2:10][C@H:9]1[CH3:36])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:37][C@@H:38]1[CH2:43][O:42][CH2:41][CH2:40][NH:39]1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([CH2:14][N:39]2[CH2:40][CH2:41][O:42][CH2:43][C@H:38]2[CH3:37])[N:11]([CH2:16][C:17]([N:19]2[C:27]3[C:22](=[N:23][CH:24]=[C:25]([C:28]([F:33])([F:32])[CH2:29][CH2:30][CH3:31])[CH:26]=3)[C:21]([CH3:35])([CH3:34])[CH2:20]2)=[O:18])[CH2:10][C@H:9]1[CH3:36])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 641498(R)-3-MethylmorpholineHCID 86724041(2R,5R)-5-chloromethyl-4-{2-[6-(1,1-difluoro-butyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-2-oxo-ethyl}-2-methyl-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 70981092(2R,5S)-4-{2-[6-(1,1-Difluoro-butyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-2-oxo-ethyl}-2-methyl-5-((R)-3-methyl-morpholin-4-ylmethyl)-piperazine-1-carboxylic acid tert-butyl ester

Procedure

Prepared from (2R,5R)-5-chloromethyl-4-{2-[6-(1,1-difluoro-butyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-2-oxo-ethyl}-2-methyl-piperazine-1-carboxylic acid tert-butyl ester and (R)-3-methyl-morpholine in a similar manner to General Procedure 6. MS: [M+H]+=594.

Sources & evidence

ORD record
ord-1230e1e5c77548f9bf5dc8fd3f3ab2ce
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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