Hydrochloric Acid → HCID 71280493, compound

HRID 246601Notes

Reaction equation

HRID 246601 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:12]3[N:13]=[C:14]4[C:20]([C:21]([NH:23][C:24]([CH3:35])([CH3:34])[CH2:25][NH:26]C(=O)OC(C)(C)C)=[O:22])=[CH:19][NH:18][C:15]4=[N:16][CH:17]=3)=[N:7][N:8]2[CH3:11])=[CH:4][CH:3]=1.Cl>O1CCOCC1>[NH2:26][CH2:25][C:24]([NH:23][C:21]([C:20]1[C:14]2[C:15](=[N:16][CH:17]=[C:12]([C:6]3[C:5]4[C:9](=[CH:10][C:2]([Cl:1])=[CH:3][CH:4]=4)[N:8]([CH3:11])[N:7]=3)[N:13]=2)[NH:18][CH:19]=1)=[O:22])([CH3:35])[CH3:34]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71280350HCID 71280350, compound

Product 1

HCID 71280493HCID 71280493, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 2-(2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamido)-2-methylpropylcarbamate (0.05 g, 0.1 mmol) in 30 mL of a saturated solution of HCl (g) in dioxane was stirred at room temperature for 2 hours. The solvent was removed and the residue was triturated with ethyl acetate, filtered and filter cake washed with saturated aqueous NaHCO3 and water successively to give N-(1-amino-2-methylpropan-2-yl)-2-(6-chloro-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (22 mg, 55%) as a yellow solid. MS: (M+H)+=398; 1H NMR (300 MHz, DMSO): δ 8.97 (s, 1H), 8.60 (d, 1H, J=8.7 Hz), 8.36 (s, 1H), 7.96 (s, 1H), 7.90 (s, 1H), 7.32 (d, 1H, J=8.7 Hz), 4.17 (s, 3H), 2.90 (s, 2H), 1.30 (s, 6H).

Workup

  1. customThe solvent was removed
  2. customthe residue was triturated with ethyl acetate
  3. filtrationfiltered
  4. filtrationfilter cake
  5. washwashed with saturated aqueous NaHCO3 and water successively

Sources & evidence

ORD record
ord-b6e6f37694e14f4eaaa0666e6c8d6374
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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