Hydrochloric Acid → HCID 118483420, compound

HRID 58460Notes

Reaction equation

HRID 58460 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[CH:12]1[CH2:17][CH2:16][N:15]([C:18]([C:20]2[C:28]3[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][C:23]=3[NH:22][N:21]=2)=[O:19])[CH2:14][CH2:13]1.[ClH:36]>C(Cl)Cl.CCOCC>[ClH:36].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[CH:12]1[CH2:17][CH2:16][N:15]([C:18]([C:20]2[C:28]3[CH2:27][CH2:26][NH:25][CH2:24][C:23]=3[NH:22][N:21]=2)=[O:19])[CH2:14][CH2:13]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118483369HCID 118483369, compound

Product 1

HCID 118483420HCID 118483420, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(4-(2-fluoro-6-(trifluoromethyl)phenyl)piperidine-1-carbonyl)-4,5-dihydro-1H pyrazolo[3,4-c]pyridine-6(7H)-carboxylate (55, 94 mg, 0.19 mmol) in CH2Cl2 (3 mL) was added HCl (2N in Et2O, 3 mL). The mixture was stirred for 18 h at ambient temperature. The reaction mixture was diluted with Et2O (20 mL) and the mixture concentrated under reduced pressure to yield (4-(2-fluoro-6-(trifluoromethyl)phenyl)piperidin-1-yl)(4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridin-3-yl)methanone hydrochloride (56) as a white solid (80 mg, 97%): 1H NMR (300 MHz, DMSO-d6) δ 9.39-9.26 (m, 2H), 7.63-7.47 (m, 3H), 4.76-4.40 (m, 1H), 4.35-4.25 (m, 2H), 3.78-3.39 (m, 4H), 3.25-3.08 (m, 2H), 2.91-2.78 (m, 3H), 2.11-1.88 (m, 2H), 1.81-1.66 (m, 2H); ESI MS m/z 397 [M+H]+.

Workup

  1. concentrationthe mixture concentrated under reduced pressure

Sources & evidence

ORD record
ord-6b3a31c2f803422297c2876f5073b932
Source dataset
uspto-grants-2016_09
Patent number
US09434727B2

Reaction notes

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