Hydrochloric Acid → N-(1-hydroxy-2-methylpropan-2-yl)-2-(6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

HRID 246686Notes

Reaction equation

HRID 246686 reaction equation
[Si]([O:8][CH2:9][C:10]([NH:13][C:14]([C:16]1[C:24]2[C:19](=[N:20][CH:21]=[C:22]([C:25]3[C:33]4[C:28](=[CH:29][C:30]([CH3:34])=[CH:31][CH:32]=4)[NH:27][N:26]=3)[N:23]=2)[NH:18][CH:17]=1)=[O:15])([CH3:12])[CH3:11])(C(C)(C)C)(C)C.Cl>O1CCOCC1>[OH:8][CH2:9][C:10]([NH:13][C:14]([C:16]1[C:24]2[C:19](=[N:20][CH:21]=[C:22]([C:25]3[C:33]4[C:28](=[CH:29][C:30]([CH3:34])=[CH:31][CH:32]=4)[NH:27][N:26]=3)[N:23]=2)[NH:18][CH:17]=1)=[O:15])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71280441N-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-(6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Product 1

HCID 71280636N-(1-hydroxy-2-methylpropan-2-yl)-2-(6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamideYield 26.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N-(1-(tert-Butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-(6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (75 mg, 0.16 mmol) was added to a saturated solution of HCl (g) in dioxane (15 mL) at room temperature and stirred for 2 hours. The reaction mixture was filtered, the filter cake washed with 2 mL of methanol, then dried at 40° C. under reduced pressure to give N-(1-hydroxy-2-methylpropan-2-yl)-2-(6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (15 mg, 26.4%) as a yellow solid. MS: (M+H)+=365; 1H NMR (300 MHz, DMSO): δ 13.34 (s, 1H), 12.76 (s, 1H), 9.14 (s, 1H), 8.46 (d, 1H, J=7.8 Hz), 8.35 (s, 1H), 7.95 (s, 1H), 7.41 (s, 1H), 7.09 (d, 1H, J=8.4 Hz), 5.05 (t, 1H, J=5.7 Hz), 3.65 (d, 1H, J=5.7 Hz), 2.50 (s, 3H), 1.46 (s, 6H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe filter cake washed with 2 mL of methanol
  3. customdried at 40° C. under reduced pressure

Sources & evidence

ORD record
ord-90483c47cca0445ebe5e254c9900ee66
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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