Hydrochloric Acid → 1-[6-(4-Fluoro-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-ylmethyl)-piperazin-1-yl]-ethanone dihydrochloride

HRID 1475526Notes

Reaction equation

HRID 1475526 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][CH:36]=4)[CH:32]=3)[C:27]([CH3:43])([CH3:42])[CH2:26]2)=[O:24])[CH2:10][C@H:9]1[CH3:44])=O)(C)(C)C.[ClH:45]>CCOC(C)=O.O1CCOCC1>[ClH:45].[ClH:45].[F:41][C:38]1[CH:39]=[CH:40][C:35]([CH2:34][C:31]2[CH:32]=[C:33]3[N:25]([C:23](=[O:24])[CH2:22][N:11]4[CH2:10][C@@H:9]([CH3:44])[NH:8][CH2:13][C@@H:12]4[CH2:14][N:15]4[CH2:20][CH2:19][O:18][CH2:17][C@H:16]4[CH3:21])[CH2:26][C:27]([CH3:43])([CH3:42])[C:28]3=[N:29][CH:30]=2)=[CH:36][CH:37]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 70980911(2R,5S)-4-{2-[6-(4-Fluoro-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

Product 1

HCID 714716131-[6-(4-Fluoro-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-ylmethyl)-piperazin-1-yl]-ethanone dihydrochloride

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

(2R,5S)-4-{2-[6-(4-Fluoro-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 (1.9 g, 3.29 mmol) was dissolved in EtOAc (48 mL) and 4 M HCl in dioxane (82 mL) and stirred at room temperature for 18 h. The solvent was removed in vacuo and resulting solid triturated with diethyl ether and dried in a vacuum oven at 40° C., to give the title compound (1.36 g). 1H NMR (DMSO-d6): 11.71-10.46 (1H, m), 10.14 (1H, s), 9.52 (1H, s), 8.31 (1H, s), 8.25 (1H, s), 7.32 (2H, dd), 7.15 (2H, t), 4.12-4.01 (4H, m), 4.01-3.56 (7H, m), 3.45 (4H, s), 3.22 (2H, d), 3.17 (2H, s), 3.09 (1H, d), 2.89 (1H, d), 1.41 (6H, s), 1.24 (6H, m). MS: [M+H]+=510.

Workup

  1. customThe solvent was removed in vacuo
  2. customresulting solid
  3. customtriturated with diethyl ether
  4. customdried in a vacuum oven at 40° C.

Sources & evidence

ORD record
ord-05517a874666442fa0b68e579ca853d5
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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