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

HRID 246716Notes

Reaction equation

HRID 246716 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][N:37]4[CH2:42][CH2:41][O:40][CH2:39][CH2:38]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:62]>O1CCOCC1>[ClH:62].[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][N:37]4[CH2:38][CH2:39][O:40][CH2:41][CH2:42]4)[N:26]=3)=[CH:23][N:24]=[C:19]2[NH:18][CH:17]=1)=[O:15])([CH3:12])[CH3:11]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71280346N-(1-(tert-butyldimethylsilyloxy)-2-methylpropan-2-yl)-2-(6-methyl-1-(2-morpholinoethyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide

Product 1

HCID 71280460N-(1-hydroxy-2-methylpropan-2-yl)-2-(6-methyl-1-(2-morpholinoethyl)-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide hydrochlorideYield 64%

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-morpholinoethyl)-1H-indazol-3-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (167 mg, 0.2 mmol) in dioxane (20 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-(2-morpholinoethyl)-1H-indazol-3-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide hydrochloride (76 mg, 64%) as a white solid. LCMS: (M+H)+=478; 1H NMR (300 MHz, CD3OD): δ 9.15 (s, 1H), 8.49 (d, 1H, J=8.4 Hz), 8.29 (s, 1H), 7.56 (s, 1H), 7.22 (d, 1H, J=8.1 Hz), 5.00-4.96 (m, 2H), 4.08-3.85 (m, 12H), 2.59 (s, 3H), 1.56 (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-d50f42095ab54f63a01d3197cf50b0d5
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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