1,4-Dioxane → (5S)-5-amino-1-[3-methyl-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperidin-2-one

HRID 57925Notes

Reaction equation

HRID 57925 reaction equation
[CH3:1][C:2]1[C:3]([N:24]2[C:29](=[O:30])[CH2:28][CH2:27][C@H:26]([NH:31]C(=O)OC(C)(C)C)[CH2:25]2)=[N:4][C:5]([N:8]2[C:16]3[CH:15]=[C:14]([C:17]4[CH:22]=[N:21][CH:20]=[C:19]([CH3:23])[N:18]=4)[N:13]=[CH:12][C:11]=3[CH:10]=[N:9]2)=[CH:6][CH:7]=1.O1CCOCC1>Cl>[NH2:31][C@@H:26]1[CH2:25][N:24]([C:3]2[C:2]([CH3:1])=[CH:7][CH:6]=[C:5]([N:8]3[C:16]4[CH:15]=[C:14]([C:17]5[CH:22]=[N:21][CH:20]=[C:19]([CH3:23])[N:18]=5)[N:13]=[CH:12][C:11]=4[CH:10]=[N:9]3)[N:4]=2)[C:29](=[O:30])[CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 312751,4-Dioxane2×HCID 86707114tert-butyl N-[(3S)-1-[3-methyl-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-6-oxo-3-piperidyl]carbamate

Product 1

HCID 86707115(5S)-5-amino-1-[3-methyl-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperidin-2-oneYield 30.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of tert-butyl N-[(3S)-1-[3-methyl-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-6-oxo-3-piperidyl]carbamate (63 mg, 0.12 mmol) in hydrogen chloride (4 mol/l) in 1,4-dioxane (2.0 ml, 8.0 mmol) and 1,4-dioxane 2.0 mL was stirred at RT 18 h. The reaction was concentrated in vacuum. The crude product was submitted for reverse phase HPLC to give 221 15 mg 29% yield. MS (ESI) m/z: 415.1. 1H NMR (400 MHz, DMSO) δ 9.61 (s, 1H), 9.48 (s, 1H), 9.35 (s, 1H), 8.73 (s, 1H), 8.64 (s, 1H), 7.98 (d, J=8.2 Hz, 1H), 7.93 (d, J=8.3 Hz, 1H), 4.27 (s, 1H), 3.86 (s, 1H), 3.59 (d, J=33.7 Hz, 1H), 3.40 (s, 1H), 2.68 (t, J=18.2 Hz, 3H), 2.20 (d, J=13.0 Hz, 3H), 2.10 (s, 1H), 1.85 (s, 2H).

Workup

  1. concentrationThe reaction was concentrated in vacuum

Sources & evidence

ORD record
ord-05265bf32a4e408d89d90d8db31bdc0c
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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