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

HRID 1475478Notes

Reaction equation

HRID 1475478 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].[F:17][C:18]([C:21]1[CH:22]=[C:23]2[NH:29][CH2:28][C:27]([CH3:31])([CH3:30])[C:24]2=[N:25][CH:26]=1)([F:20])[CH3:19].Cl[CH2:33][C:34](Cl)=[O:35].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]([CH2:33][C:34]([N:29]2[C:23]3[C:24](=[N:25][CH:26]=[C:21]([C:18]([F:20])([F:17])[CH3:19])[CH:22]=3)[C:27]([CH3:31])([CH3:30])[CH2:28]2)=[O:35])[CH2:10][C@H:9]1[CH3:16])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 709800546-(1,1-difluoro-ethyl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridineHCID 71003242(2R,5R)-tert-Butyl 5-(hydroxymethyl)-2-methylpiperazine-1-carboxylate

Product 1

HCID 70980183(2R,5R)-4-{2-[6-(1,1-Difluoro-ethyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-2-oxo-ethyl}-5-hydroxymethyl-2-methyl-piperazine-1-carboxylic acid tert-butyl esterYield 60.9%

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 (1.74 g, 7.5 mmol), 6-(1,1-difluoro-ethyl)-3,3-dimethyl-2,3-dihydro-1H-pyrrolo[3,2-b]pyridine (1.1 g, 5.0 mmol), chloroacetyl chloride (490 μL, 6.1 mmol) and DIPEA (3 mL, 16.6 mmol) to give the title compound (1.47 g) as an orange semi-solid. MS: [M+H]+=483.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-1dabeb38c7af4f60b1a93514496016a8
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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