Hydrochloric Acid → 1-[6-(4,4-Difluoro-3-piperidyl)-2-pyridyl]-6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridine

HRID 57976Notes

Reaction equation

HRID 57976 reaction equation
[F:1][C:2]1([F:37])[CH2:7][CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4][CH:3]1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N:21]2[C:29]3[CH:28]=[C:27]([C:30]4[CH:35]=[N:34][CH:33]=[C:32]([CH3:36])[N:31]=4)[N:26]=[CH:25][C:24]=3[CH:23]=[N:22]2)[N:16]=1.O1CCOCC1.Cl>>[F:37][C:2]1([F:1])[CH2:7][CH2:6][NH:5][CH2:4][CH:3]1[C:15]1[N:16]=[C:17]([N:21]2[C:29]3[CH:28]=[C:27]([C:30]4[CH:35]=[N:34][CH:33]=[C:32]([CH3:36])[N:31]=4)[N:26]=[CH:25][C:24]=3[CH:23]=[N:22]2)[CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-Dioxane2×HCID 86707158Tert-butyl 4,4-difluoro-3-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperidine-1-carboxylate

Product 1

HCID 727147641-[6-(4,4-Difluoro-3-piperidyl)-2-pyridyl]-6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridineYield 42.1%

Procedure

To a solution of tert-butyl 4,4-difluoro-3-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperidine-1-carboxylate (50 mg, 0.099 mmol) in 1,4-DIOXANE (2.00 mL, 23.4 mmol) was added hydrogen chloride (4 mol/l) in 1,4-dioxane (1.00 mL, 4.00 mmol). The reaction was stirred at RT 18 h. The reaction was concentrated and submitted for reverse phase HPLC to give 259 17 mg 42% yield. MS (ESI) m/z: 408.1. 1H NMR (400 MHz, DMSO) δ 9.72 (s, 1H), 9.46 (s, 1H), 9.36 (s, 1H), 8.74 (s, 1H), 8.63 (s, 1H), 8.04 (t, J=7.8 Hz, 1H), 7.98 (d, J=8.2 Hz, 1H), 7.40 (d, J=7.4 Hz, 1H), 3.60-3.42 (m, 2H), 3.18 (d, J=12.8 Hz, 1H), 2.87 (t, J=12.6 Hz, 1H), 2.67 (s, 3H), 2.36 (d, J=18.3 Hz, 1H), 2.21-2.09 (m, 1H), 1.99 (d, J=34.4 Hz, 1H).

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-533bda55a8994401bcc797fbbaef3cff
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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