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

HRID 246694
Notes
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Reaction equation

HRID 246694 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][CH2:36][CH2:37][N:38]4[CH2:43][CH2:42][O:41][CH2:40][CH2:39]4)[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][CH2:36][CH2:37][N:38]4[CH2:39][CH2:40][O:41][CH2:42][CH2:43]4)[N:26]=3)=[CH:23][N:24]=[C:19]2[NH:18][CH:17]=1)=[O:15])([CH3:12])[CH3:11]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71279557N-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-(6-methyl-1-(3-morpholinopropyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

Product 1

HCID 71279628N-(1-hydroxy-2-methylpropan-2-yl)-2-(6-methyl-1-(3-morpholinopropyl)-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide hydrochlorideYield 71%

Reagents, catalysts & solvents 1

HCID 31275
1,4-Dioxane
Solvent

Procedure

To a stirred solution of N-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-(6-methyl-1-(3-morpholinopropyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (95 mg, 0.112 mmol) in dioxane (40 mL) was bubbled HCl gas until saturation and then stirred at room temperature for 16 hours. Reaction mixture was concentrated and the residue was triturated with methanol (1 mL) then decanted and dried to afford N-(1-hydroxy-2-methylpropan-2-yl)-2-(6-methyl-1-(3-morpholinopropyl)-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide hydrochloride (42 mg, 71%) as a yellow solid. LCMS: (M+H)+=492; 1H NMR (300 MHz, DMSO+D2O): δ 9.14 (s, 1H), 8.44 (d, 1H, J=8.1 Hz), 8.36 (s, 1H), 7.59 (s, 1H), 7.17 (d, 1H, J=8.4 Hz), 4.59-4.56 (m, 2H), 4.03-3.99 (m, 2H), 3.78-3.75 (m, 4H), 3.43-3.18 (m, 6H), 2.54 (s, 3H), 2.36 (brs, 2H), 1.43 (s, 6H).

Workup

  1. customReaction mixture
  2. concentrationwas concentrated
  3. customthe residue was triturated with methanol (1 mL)
  4. customthen decanted
  5. customdried

Sources & evidence

ORD record
ord-212c016383954488822d264d2aa565cf
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08658646B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes