Hydrochloric Acid → 1-[6-(1,1-Difluoro-butyl)-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 1475527Notes

Reaction equation

HRID 1475527 reaction equation
[ClH:1].C(OC([N:9]1[CH2:14][C@H:13]([CH2:15][N:16]2[CH2:21][CH2:20][O:19][CH2:18][C@H:17]2[CH3:22])[N:12]([CH2:23][C:24]([N:26]2[C:34]3[C:29](=[N:30][CH:31]=[C:32]([C:35]([F:40])([F:39])[CH2:36][CH2:37][CH3:38])[CH:33]=3)[C:28]([CH3:42])([CH3:41])[CH2:27]2)=[O:25])[CH2:11][C@H:10]1[CH3:43])=O)(C)(C)C>O1CCOCC1.CCOC(C)=O>[ClH:1].[ClH:1].[F:39][C:35]([C:32]1[CH:33]=[C:34]2[N:26]([C:24](=[O:25])[CH2:23][N:12]3[CH2:11][C@@H:10]([CH3:43])[NH:9][CH2:14][C@@H:13]3[CH2:15][N:16]3[CH2:21][CH2:20][O:19][CH2:18][C@H:17]3[CH3:22])[CH2:27][C:28]([CH3:42])([CH3:41])[C:29]2=[N:30][CH:31]=1)([F:40])[CH2:36][CH2:37][CH3:38]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 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

Product 1

HCID 714718871-[6-(1,1-Difluoro-butyl)-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

4N HCl in dioxane (35 mL) was added to a solution of (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 (2.1 g) in EtOAc (10 mL). The resulting suspension was stirred for 1 h at room temperature. The solvent was then removed in vacuo. The solid was triturated in Et2O, collected by filtration, washed with Et2O and dried in vacuo to give the title compound (1.7 g) as a yellow solid. 1H NMR (Me-d3-OD): 8.77 (1H, s), 8.52 (1H, s), 4.36-3.91 (9H, m), 3.91-3.41 (8H, m), 3.18-2.99 (1H, m), 2.34-2.15 (2H, m), 1.67-1.36 (15H, m), 1.00 (3H, t). MS: [M+H]+=494.

Workup

  1. customThe solvent was then removed in vacuo
  2. customThe solid was triturated in Et2O
  3. filtrationcollected by filtration
  4. washwashed with Et2O
  5. customdried in vacuo

Sources & evidence

ORD record
ord-2fc7fab0e4f049989f15924abb26c7f3
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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