Hydrochloric Acid → HCID 71279915, compound

HRID 246688Notes

Reaction equation

HRID 246688 reaction equation
[CH3:1][C:2]([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])[CH2:3][NH:4]C(=O)OC(C)(C)C.[ClH:35]>C(OCC)(=O)C>[ClH:35].[NH2:4][CH2:3][C:2]([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])([CH3:1])[CH3:12]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71280571tert-butyl 2-methyl-2-(2-(6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamido)propylcarbamate

Product 1

HCID 71279915HCID 71279915, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 2-methyl-2-(2-(6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamido)propylcarbamate (100 mg, 0.22 mmol) was added to a saturated solution of HCl gas in ethyl acetate (20 mL) and the mixture was stirred at room temperature for 3 hours. The solid obtained was filtered and washed with 5 mL of ethyl acetate to give N-(1-amino-2-methylpropan-2-yl)-2-(6-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide hydrochloride (25 mg, 32%) as a yellow solid. MS: (M+H)+=364; 1H NMR (300 MHz, DMSO): δ 13.45 (s, 1H), 12.96 (s, 1H), 9.19 (s, 1H), 8.47-8.40 (m, 2H), 8.12-8.10 (m, 3H), 7.46 (s, 1H), 7.12 (d, 1H, J=8.4 Hz), 3.84 (brs, 5H), 3.42 (d, 2H, J=4.8 Hz), 2.52 (s, 3H), 1.58 (s, 3H).

Workup

  1. customThe solid obtained
  2. filtrationwas filtered
  3. washwashed with 5 mL of ethyl acetate

Sources & evidence

ORD record
ord-b3e53c89d1fa489a8d71ad646f48e36e
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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