Hydrochloric Acid → HCID 118483553, compound

HRID 58451Notes

Reaction equation

HRID 58451 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:32]([F:35])([F:34])[F:33])=[C:6]([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:7]=1.[ClH:36]>C(Cl)Cl.CCOCC>[ClH:36].[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:32]([F:35])([F:33])[F:34])=[C:6]([CH:8]2[CH2:13][CH2:12][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])[CH2:10][CH2:9]2)[CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 118483434tert-butyl 3-(4-(5-fluoro-2-(trifluoromethyl)phenyl) piperidine-1-carbonyl)-6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate

Product 1

HCID 118483553HCID 118483553, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(4-(5-fluoro-2-(trifluoromethyl)phenyl)piperidine-1-carbonyl)-6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate (45, 120 mg, 0.24 mmol) in CH2Cl2 (2 mL) was added HCl (2N in Et2O, 2 mL). The mixture stirred for 18 h at ambient temperature. Additional HCl (2N in Et2O, 1 mL) was added and the mixture was stirred at ambient temperature for 3 h. The reaction mixture was diluted with Et2O (20 mL) and the resulting solids were collected by filtration to provide (4-(5-fluoro-2-(trifluoromethyl)phenyl)piperidin-1-yl)(4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl)methanone hydrochloride (46) as a white solid (104 mg, 99%): 1H NMR (300 MHz, DMSO-d6) δ 9.54-9.19 (m, 2H), 7.84 (dd, J=9.0, 5.7 Hz, 1H), 7.60-7.51 (m, 1H), 7.32-7.20 (m, 1H), 5.32-5.12 (m, 1H), 4.78-4.60 (m, 1H), 4.29-4.16 (m, 2H), 3.43-3.30 (m, 2H, overlaps with H2O), 3.26-3.06 (m, 2H), 2.95 (t, J=5.4 Hz, 2H), 2.89-2.72 (m, 1H), 1.84-1.65 (m, 4H) missing N—H pyrazole; ESI MS m/z 397 [M+H]+.

Workup

  1. stirringthe mixture was stirred at ambient temperature for 3 h
  2. filtrationthe resulting solids were collected by filtration

Sources & evidence

ORD record
ord-300ad844644c497b8c40e691e2510d12
Source dataset
uspto-grants-2016_09
Patent number
US09434727B2

Reaction notes

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