Chloroacetyl chloride → (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

HRID 1475479Notes

Reaction equation

HRID 1475479 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([CH2:14][OH:15])[NH:11][CH2:10][C@H:9]1[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[F:18][C:19]([F:37])([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:20]1[N:25]=[CH:24][C:23]2[C:26]([CH3:30])([CH3:29])[CH2:27][NH:28][C:22]=2[CH:21]=1.Cl[CH2:39][C:40](Cl)=[O:41].CCN(C(C)C)C(C)C>>[C:1]([O:5][C:6]([N:8]1[CH2:13][C@H:12]([CH2:14][OH:15])[N:11]([CH2:39][C:40]([N:28]2[C:22]3[CH:21]=[C:20]([C:19]([F:18])([F:37])[C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:25]=[CH:24][C:23]=3[C:26]([CH3:30])([CH3:29])[CH2:27]2)=[O:41])[CH2:10][C@H:9]1[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 709811026-(Difluoro-phenyl-methyl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine hydrochlorideHCID 71003242(2R,5R)-tert-Butyl 5-(hydroxymethyl)-2-methylpiperazine-1-carboxylate

Product 1

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 esterYield 78.6%

Procedure

The title compound was prepared following methods similar to those described in Preparation 203 starting from (2R,5R)-5-hydroxymethyl-2-methyl-piperazine-1-carboxylic acid tert-butyl ester (1.1 g, 3.2 mmol), 6-(difluoro-phenyl-methyl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-c]pyridine hydrochloride (1.0 g, 3.55 mmol), chloroacetyl chloride (282 μL, 3.55 mmol) and DIPEA (2 mL, 11.3 mmol) to give the title compound (1.37 g) as an orange gum. MS: [M+H]+=545.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-8acd0d48f5c24003bff56217410500e8
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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