Hydrochloric Acid → 1-[6-(2,4-Difluoro-benzyl)-3,3-dimethyl-2,3-dihydro-pyrrolo[3,2-b]pyridin-1-yl]-2-[(2R,5R)-5-methyl-2-((R)-3-methyl-morpholin-4-yl methyl)-piperazin-1-yl]-ethanone, dihydrochloride

HRID 1475532Notes

Reaction equation

C(OC([N:8]1[CH2:13][C@H:12]([CH2:14][N:15]2[CH2:20][CH2:19][O:18][CH2:17][C@H:16]2[CH3:21])[N:11]([CH2:22][C:23]([N:25]2[C:33]3[C:28](=[N:29][CH:30]=[C:31]([CH2:34][C:35]4[CH:40]=[CH:39][C:38]([F:41])=[CH:37][C:36]=4[F:42])[CH:32]=3)[C:27]([CH3:44])([CH3:43])[CH2:26]2)=[O:24])[CH2:10][C@H:9]1[CH3:45])=O)(C)(C)C.C(OCC)(=O)C.[ClH:52]>O1CCOCC1>[ClH:52].[ClH:52].[F:42][C:36]1[CH:37]=[C:38]([F:41])[CH:39]=[CH:40][C:35]=1[CH2:34][C:31]1[CH:32]=[C:33]2[N:25]([C:23](=[O:24])[CH2:22][N:11]3[CH2:10][C@@H:9]([CH3:45])[NH:8][CH2:13][C@@H:12]3[CH2:14][N:15]3[CH2:20][CH2:19][O:18][CH2:17][C@H:16]3[CH3:21])[CH2:26][C:27]([CH3:44])([CH3:43])[C:28]2=[N:29][CH:30]=1

Participants

Conditions

Temperature: 20 °C

Procedure

A mixture of (2R,5S)-4-{2-[6-(2,4-difluoro-benzyl)-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 (0.103 g), ethyl acetate (10 mL) and 4 M HCl in dioxan (10 mL) was stirred at 20° C. for 18 h and the resulting solid collected by filtration to give the title compound (0.075 g). 1H NMR (Me-d3-OD): 8.76 (1H, s), 8.48 (1H, s), 7.56-7.44 (1H, m), 7.11-6.98 (2H, m), 4.27 (5H, d), 4.16-3.96 (5H, m), 3.82 (3H, s), 3.66-3.41 (5H, m), 3.18 (4H, d), 1.62 (6H, s), 1.41 (6H, br m). MS: [M+H]+=528.

Workup

filtrationthe resulting solid collected by filtration

Sources & evidence

ORD record: ord-8967a6eb21344d8487102bb6931ecc2e
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09018214B2

Reaction notes

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