1,4-Dioxane → HCID 178430471, compound

HRID 57928Notes

Reaction equation

HRID 57928 reaction equation
C[O:2][C:3]1[C:4]([N:25]2[CH2:30][CH2:29][CH2:28][C@H:27]([NH:31]C(=O)OC(C)(C)C)[CH2:26]2)=[N:5][C:6]([N:9]2[C:17]3[CH:16]=[C:15]([C:18]4[CH:23]=[N:22][CH:21]=[C:20]([CH3:24])[N:19]=4)[N:14]=[CH:13][C:12]=3[CH:11]=[N:10]2)=[CH:7][N:8]=1.O1CCOCC1>Cl>[NH2:31][C@H:27]1[CH2:28][CH2:29][CH2:30][N:25]([C:4]2[C:3]([OH:2])=[N:8][CH:7]=[C:6]([N:9]3[C:17]4[CH:16]=[C:15]([C:18]5[CH:23]=[N:22][CH:21]=[C:20]([CH3:24])[N:19]=5)[N:14]=[CH:13][C:12]=4[CH:11]=[N:10]3)[N:5]=2)[CH2:26]1

Participants

4

Reactant 2

HCID 312751,4-Dioxane2×HCID 86707116tert-butyl N-[(3S)-1-[3-methoxy-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]pyrazin-2-yl]-3-piperidyl]carbamate

Product 1

HCID 178430471HCID 178430471, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of tert-butyl N-[(3S)-1-[3-methoxy-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]pyrazin-2-yl]-3-piperidyl]carbamate (30 mg, 0.058 mmol) in hydrogen chloride (4 mol/l) in 1,4-dioxane (1.0 ml, 4.0 mmol) and 1,4-dioxane 1.0 mL was stirred at RT 2d. The reaction was concentrated and submitted for reverse phase HPLC to give 223 (7 mg, 27% yield. MS (ESI) m/z: 404.1. 1H NMR (400 MHz, DMSO) δ 9.44 (s, 1H), 9.28 (s, 1H), 9.25 (s, 1H), 8.61 (s, 1H), 8.57 (s, 1H), 7.23 (s, 1H), 4.74 (d, J=11.1 Hz, 1H), 4.44 (d, J=12.8 Hz, 1H), 2.92 (s, 2H), 2.62 (s, 3H), 1.88 (d, J=16.7 Hz, 2H), 1.68 (d, J=11.1 Hz, 1H), 1.39 (d, J=9.5 Hz, 1H).

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-db082c90d5ed48fc935fd56a7696aa00
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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