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

HRID 246696Notes

Reaction equation

HRID 246696 reaction equation
[Si]([O:8][CH2:9][C:10]([NH:13][C:14]([C:16]1[C:20]2=[N: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][C:36]([N:38]4[CH2:43][CH2:42][O:41][CH2:40][CH2:39]4)=[O:37])[N:26]=3)=[CH:23][N:24]=[C:19]2[N:18](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:17]=1)=[O:15])([CH3:12])[CH3:11])(C(C)(C)C)(C)C.[ClH:63]>O1CCOCC1>[ClH:63].[OH:8][CH2:9][C:10]([NH:13][C:14]([C:16]1[C:20]2=[N: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][C:36]([N:38]4[CH2:43][CH2:42][O:41][CH2:40][CH2:39]4)=[O:37])[N:26]=3)=[CH:23][N:24]=[C:19]2[NH:18][CH:17]=1)=[O:15])([CH3:11])[CH3:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71280327N-(1-(tert-Butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-(6-methyl-1-(2-morpholino-2-oxoethyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

Product 1

HCID 71280331N-(1-hydroxy-2-methylpropan-2-yl)-2-(6-methyl-1-(2-morpholino-2-oxoethyl)-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide hydrochlorideYield 71%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of N-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-(6-methyl-1-(2-morpholino-2-oxoethyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (100 mg, 0.118 mmol) in dioxane (40 mL) was bubbled HCl gas until saturation and then stirred at room temperature for 16 hours. The mixture was concentrated and the residue was triturated with methanol (1 mL), solvent decanted and solid dried to afford N-(1-hydroxy-2-methylpropan-2-yl)-2-(6-methyl-1-(2-morpholino-2-oxoethyl)-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide hydrochloride (44 mg, 71%) as a yellow solid. LCMS: (M+H)+=492; 1H NMR (300 MHz, DMSO+D2O): δ 9.07 (s, 1H), 8.44 (d, 1H, J=8.4 Hz), 8.36 (s, 1H), 7.45 (s, 1H), 7.15 (d, 1H, J=8.4 Hz), 5.55 (s, 2H), 3.72-3.65 (m, 8H), 3.47 (brs, 2H), 2.53 (s, 3H), 2.36 (brs, 2H), 1.46 (s, 6H).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was triturated with methanol (1 mL), solvent
  3. customdecanted
  4. customsolid dried

Sources & evidence

ORD record
ord-63680dc21c494411bc1e89443fecb230
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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