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

HRID 246699Notes

Reaction equation

HRID 246699 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)[N:27]([CH2:35][CH2:36][CH2:37][N:38]([CH3:40])[CH3:39])[N:26]=3)[N:23]=2)[NH:18][CH:17]=1)=[O:15])([CH3:12])[CH3:11])(C(C)(C)C)(C)C.[ClH:41]>CO>[ClH:41].[CH3:40][N:38]([CH3:39])[CH2:37][CH2:36][CH2:35][N:27]1[C:28]2[C:33](=[CH:32][CH:31]=[C:30]([CH3:34])[CH:29]=2)[C:25]([C:22]2[N:23]=[C:24]3[C:16]([C:14]([NH:13][C:10]([CH3:11])([CH3:12])[CH2:9][OH:8])=[O:15])=[CH:17][NH:18][C:19]3=[N:20][CH:21]=2)=[N:26]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71280324N-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-(1-(3-(dimethylamino)propyl)-6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Product 1

HCID 712801272-(1-(3-(dimethylamino)propyl)-6-methyl-1H-indazol-3-yl)-N-(1-hydroxy-2-methylpropan-2-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of N-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-(1-(3-(dimethylamino)propyl)-6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (1 g, 1.78 mmol) in 10 mL of methanol was added 1 mL of concentrated HCl, stirred for 3 hours, the precipitate was filtered and the filter cake was washed with 2-methoxy-2-methylpropane to give 25 mg of 2-(1-(3-(dimethylamino)propyl)-6-methyl-1H-indazol-3-yl)-N-(1-hydroxy-2-methylpropan-2-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide hydrochloride. LCMS: (M+H)+=450; 1H NMR (300 MHz, DMSO): δ 12.84 (s, 1H), 9.55 (s, 1H), 9.14 (s, 1H), 8.49 (d, 1H, J=8.1 Hz), 8.40 (s, 1H), 7.96 (s, 1H), 7.62 (s, 1H), 7.17 (d, 1H, J=8.4 Hz), 4.61-4.58 (m, 2H), 3.67 (s, 2H), 3.21 (s, 2H), 2.82 (s, 6H), 2.55 (s, 3H), 2.33 (brs, 2H), 1.49 (s, 6H).

Workup

  1. filtrationthe precipitate was filtered
  2. washthe filter cake was washed with 2-methoxy-2-methylpropane

Sources & evidence

ORD record
ord-2721343b28c7476482bf2bc7f1e1a44c
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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