Hydrochloric Acid → HCID 118483399, compound

HRID 58440Notes

Reaction equation

HRID 58440 reaction equation
[F:1][C:2]1[C:3]([C:32]([F:35])([F:34])[F:33])=[C:4]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[C:20]4[CH2:21][N:22](C(OC(C)(C)C)=O)[CH2:23][CH2:24][C:19]=4[NH:18][N:17]=3)=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.[ClH:36]>C(Cl)Cl.CCOCC>[ClH:36].[F:1][C:2]1[C:3]([C:32]([F:35])([F:33])[F:34])=[C:4]([CH:8]2[CH2:9][CH2:10][N:11]([C:14]([C:16]3[C:20]4[CH2:21][NH:22][CH2:23][CH2:24][C:19]=4[NH:18][N:17]=3)=[O:15])[CH2:12][CH2:13]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118483392HCID 118483392, compound

Product 1

HCID 118483399HCID 118483399, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(4-(3-fluoro-2-(trifluoromethyl)phenyl)piperidine-1-carbonyl)-6,7-dihydro-H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate (31, 0.148 g, 0.30 mmol) in CH2Cl2 (2 mL) was added HCl (2 mL, 2.0 N solution in Et2O). The mixture stirred at ambient temperature for 18 h, was diluted with Et2O (30 mL), and the resulting solids were collected by filtration to give (4-(3-fluoro-2-(trifluoromethyl)phenyl)piperidin-1-yl)(4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl)methanone hydrochloride (32) as a white solid (0.097 g, 75%): 1H NMR (300 MHz, DMSO-d6) δ 9.46-9.20 (m, 2H), 7.74-7.61 (m, 1H), 7.46 (d, J=8.1 Hz, 1H), 7.37-7.25 (m, 1H), 4.70-4.44 (m, 2H), 4.34-4.22 (m, 2H), 3.50-3.10 (m, 4H), 2.93-2.76 (m, 3H), 1.86-1.60 (m, 4H); ESI MS m/z 468 [M+H]+.

Workup

  1. filtrationthe resulting solids were collected by filtration

Sources & evidence

ORD record
ord-afd6e3cd6847438db520ca29a686aeaf
Source dataset
uspto-grants-2016_09
Patent number
US09434727B2

Reaction notes

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