1,4-Dioxane → (3S)-1-[3-methyl-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]pyrazin-2-yl]piperidin-3-amine

HRID 57942Notes

Reaction equation

HRID 57942 reaction equation
[CH3:1][C:2]1[C:3]([N:24]2[CH2:29][CH2:28][CH2:27][C@H:26]([NH:30]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][N:7]=1.O1CCOCC1>Cl>[CH3:1][C:2]1[C:3]([N:24]2[CH2:29][CH2:28][CH2:27][C@H:26]([NH2:30])[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][N:7]=1

Participants

4

Reactant 2

HCID 312751,4-Dioxane2×HCID 86707127tert-butyl N-[(3S)-1-[3-methyl-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]pyrazin-2-yl]-3-piperidyl]carbamate

Product 1

HCID 72714574(3S)-1-[3-methyl-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]pyrazin-2-yl]piperidin-3-amineYield 56%

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]pyrazin-2-yl]-3-piperidyl]carbamate (34 mg, 0.068 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 crude product was submitted for reverse phase HPLC to give 228 (15 mg, 56% yield). MS (ESI) m/z: 402.2. 1H NMR (400 MHz, DMSO) δ 9.58 (s, 1H), 9.44 (s, 1H), 9.32 (s, 1H), 8.71 (s, 1H), 8.66 (s, 1H), 8.63 (s, 1H), 3.67 (d, J=12.3 Hz, 2H), 3.19 (t, J=11.3 Hz, 1H), 2.93 (s, 1H), 2.73 (dd, J=12.1, 9.1 Hz, 1H), 2.64 (s, 3H), 2.54 (s, 3H), 1.94 (d, J=10.2 Hz, 2H), 1.74 (d, J=11.1 Hz, 1H), 1.39-1.26 (m, 1H).

Sources & evidence

ORD record
ord-962f508b432948b892bb3467863a9519
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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