Hydrochloric Acid → (4-(2-chloro-3-fluorophenyl)piperidin-1-yl)(4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl)methanone hydrochloride

HRID 58447Notes

Reaction equation

HRID 58447 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][CH2:13][N:12]([C:15]([C:17]2[C:21]3[CH2:22][N:23](C(OC(C)(C)C)=O)[CH2:24][CH2:25][C:20]=3[NH:19][N:18]=2)=[O:16])[CH2:11][CH2:10]1.Cl>C(Cl)Cl.CCOCC>[ClH:1].[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:10][CH2:11][N:12]([C:15]([C:17]2[C:21]3[CH2:22][NH:23][CH2:24][CH2:25][C:20]=3[NH:19][N:18]=2)=[O:16])[CH2:13][CH2:14]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 118483431tert-butyl 3-(4-(2-chloro-3-fluorophenyl)piperidine-1-carbonyl)-6,7-dihydro-1Hpyrazolo[4,3-c]pyridine-5(4H)-carboxylate

Product 1

HCID 118483460(4-(2-chloro-3-fluorophenyl)piperidin-1-yl)(4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl)methanone hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(4-(2-chloro-3-fluorophenyl)piperidine-1-carbonyl)-6,7-dihydro-1H-pyrazolo[4,3-c]pyridine-5(4H)-carboxylate (41, 125 mg, 0.27 mmol) in CH2Cl2 (2 mL) was added HCl (2.0 N solution in Et2O, 2 mL). The mixture was stirred for 18 h at ambient temperature. The reaction mixture was diluted with Et2O (20 mL) and the resulting solids were collected by filtration to give (4-(2-chloro-3-fluorophenyl)piperidin-1-yl)(4,5,6,7-tetrahydro-1H-pyrazolo[4,3-c]pyridin-3-yl)methanone hydrochloride as a white solid (42, 93 mg, 86%): 1H NMR (300 MHz, DMSO-d6) δ 9.37 (br s, 2H), 7.42-7.21 (m, 3H), 5.31-5.13 (m, 1H), 4.74-4.57 (m, 1H), 4.25-4.14 (m, 2H), 3.44-3.14 (m, 4H, overlaps with H2O), 3.00-2.75 (m, 3H), 1.93-1.77 (m, 2H), 1.70-1.47 (m, 2H) missing N—H pyrazole; ESI MS m/z 363 [M+H]+.

Workup

  1. filtrationthe resulting solids were collected by filtration

Sources & evidence

ORD record
ord-98b37298c7d04183a76374b80f8455a9
Source dataset
uspto-grants-2016_09
Patent number
US09434727B2

Reaction notes

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