Hydrochloric Acid → (R)-(3-aminopiperidin-1-yl)(1-methyl-2-(1-(2,2,2-trifluoroethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-1H-benzo[d]imidazol-5-yl)methanone hydrochloride

HRID 2275038Notes

Reaction equation

HRID 2275038 reaction equation
[ClH:1].[NH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([C:11]2[CH:34]=[CH:33][C:14]3[N:15]([CH3:32])[C:16]([C:18]4[N:26]([CH2:27][C:28]([F:31])([F:30])[F:29])[C:21]5=[N:22][CH:23]=[CH:24][CH:25]=[C:20]5[CH:19]=4)=[N:17][C:13]=3[CH:12]=2)=[O:10])[CH2:4]1>CO.C(OCC)C>[ClH:1].[NH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([C:11]2[CH:34]=[CH:33][C:14]3[N:15]([CH3:32])[C:16]([C:18]4[N:26]([CH2:27][C:28]([F:31])([F:30])[F:29])[C:21]5=[N:22][CH:23]=[CH:24][CH:25]=[C:20]5[CH:19]=4)=[N:17][C:13]=3[CH:12]=2)=[O:10])[CH2:4]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 73052773(R)-(3-Aminopiperidin-1-yl)(1-methyl-2-(1-(2,2,2-trifluoroethyl)-1H-pyrrolo[2,3-b]-pyridin-2-yl)-1H-benzo[d]imidazol-5-yl)methanone

Product 1

HCID 118158907(R)-(3-aminopiperidin-1-yl)(1-methyl-2-(1-(2,2,2-trifluoroethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-1H-benzo[d]imidazol-5-yl)methanone hydrochlorideYield 99%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent2×

Procedure

HCl in Et2O (1 M) (0.15 mL, 0.15 mmol) was added dropwise to a solution of (R)-(3-aminopiperidin-1-yl)(1-methyl-2-(1-(2,2,2-trifluoroethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-1H-benzo[d]imidazol-5-yl)methanone (60 mg, 0.13 mmol) in methanol (1 mL) and diethyl ether (1 mL). After stirring for 2.5 h at rt, the reaction mixture was dried under a stream of nitrogen to give the required product (R)-(3-aminopiperidin-1-yl)(1-methyl-2-(1-(2,2,2-trifluoroethyl)-1H-pyrrolo[2,3-b]pyridin-2-yl)-1H-benzo[d]imidazol-5-yl)methanone hydrochloride (64 mg, 0.13 mmol, 99% yield).

Workup

  1. customthe reaction mixture was dried under a stream of nitrogen

Sources & evidence

ORD record
ord-1d232d3b7cf04f6b88fd6b2ea3a196a2
Source dataset
uspto-grants-2015_09
Patent number
US09127003B2

Reaction notes

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