Hydrochloric Acid → HCID 118483549, compound

HRID 58491Notes

Reaction equation

HRID 58491 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[C:24]4[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][C:19]=4[NH:18][N:17]=3)=[O:15])[CH2:10][CH2:9]2)=[C:4]([C:32]([F:35])([F:34])[F:33])[CH:3]=1.[ClH:36]>C(Cl)Cl.CO>[ClH:36].[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([C:16]3[C:24]4[CH2:23][CH2:22][NH:21][CH2:20][C:19]=4[NH:18][N:17]=3)=[O:15])[CH2:10][CH2:9]2)=[C:4]([C:32]([F:35])([F:33])[F:34])[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118483391HCID 118483391, compound

Product 1

HCID 118483549HCID 118483549, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(4-(4-fluoro-2-(trifluoromethyl)phenyl)piperidine-1-carbonyl)-4,5-dihydro-1H-pyrazolo[3,4-c]pyridine-6(7H)-carboxylate (74 mg, 0.15 mmol) in CH2Cl2 (3 mL) and methanol (1 mL) was added 2 N HCl (2 mL, 2M in Et2O). The mixture stirred for 4 h at ambient temperature. The reaction mixture was diluted with Et20 (30 mL) and the resulting solids were collected by filtration to give (4-(4-fluoro-2-(trifluoromethyl)phenyl)piperidin-1-yl)(4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridin-3-yl)methanone hydrochloride as a white solid (64 mg, 98%): 1H NMR (300 MHz, DMSO-d6) δ 13.14 (s, 1H), 9.16 (br s, 2H), 7.73-7.68 (m, 1H), 7.59-7.50 (m, 2H), 4.84-4.69 (m, 1H), 4.32-4.25 (m, 2H), 3.26-3.03 (m, 2H), 2.89-2.81 (m, 2H), 2.68-2.48 (m, 4H), 1.73 (m, 4H); ESI MS m/z 397 [M+H]+.

Workup

  1. additionThe reaction mixture was diluted with Et20 (30 mL)
  2. filtrationthe resulting solids were collected by filtration

Sources & evidence

ORD record
ord-538e9b1159c2440fb58530f02d70f9cd
Source dataset
uspto-grants-2016_09
Patent number
US09434727B2

Reaction notes

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