Hydrochloric Acid → (4-(3,5-Bis(trifluoromethyl)phenyl)piperidin-1-yl)(4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridin-3-yl)methanone Hydrochloride

HRID 58457Notes

Reaction equation

HRID 58457 reaction equation
[F:1][C:2]([F:38])([F:37])[C:3]1[CH:4]=[C:5]([CH:13]2[CH2:18][CH2:17][N:16]([C:19]([C:21]3[C:29]4[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][C:24]=4[NH:23][N:22]=3)=[O:20])[CH2:15][CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[ClH:39]>C(Cl)Cl.CCOCC>[ClH:39].[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([CH:13]2[CH2:18][CH2:17][N:16]([C:19]([C:21]3[C:29]4[CH2:28][CH2:27][NH:26][CH2:25][C:24]=4[NH:23][N:22]=3)=[O:20])[CH2:15][CH2:14]2)[CH:4]=[C:3]([C:2]([F:1])([F:37])[F:38])[CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118483437tert-butyl 3-(4-(3,5-bis(trifluoromethyl)phenyl)piperidine-1-carbonyl)-4,5-dihydro-1H-pyrazolo[3,4-c]pyridine-6(7H)-carboxylate

Product 1

HCID 118483484(4-(3,5-Bis(trifluoromethyl)phenyl)piperidin-1-yl)(4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridin-3-yl)methanone HydrochlorideYield 99%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(4-(3,5-bis(trifluoromethyl)phenyl)piperidine-1-carbonyl)-4,5-dihydro-1H-pyrazolo[3,4-c]pyridine-6(7H)-carboxylate (51, 75 mg, 0.14 mmol) in CH2Cl2 (1 mL) was added HCl (2N in Et2O, 1 mL). The mixture stirred for 18 h at ambient temperature. The reaction mixture was diluted with Et2O (50 mL) and concentrated to yield (4-(3,5-bis(trifluoromethyl)phenyl)piperidin-1-yl)(4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridin-3-yl)methanone hydrochloride (52) as a yellow solid (79 mg, >99%): 1H NMR (300 MHz, DMSO-d6) δ 9.37 (br s, 2H), 8.05-7.86 (m, 3H), 4.75-4.44 (m, 2H), 4.39-4.18 (m, 2H), 3.42-3.25 (m, 2H, overlaps with H2O), 3.20-3.03 (m, 2H), 2.95-2.75 (m, 3H), 2.03-1.80 (m, 2H), 1.79-1.62 (m, 2H), missing N—H pyrazole; ESI MS m/z 447 [M+H]+.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-811f02439ead40a4887c804377ad26d5
Source dataset
uspto-grants-2016_09
Patent number
US09434727B2

Reaction notes

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