Hydrochloric Acid → HCID 71280320, compound

HRID 246744Notes

Reaction equation

HRID 246744 reaction equation
[C:1]([NH:5][C:6]([C:8]1[C:12]2=[N:13][C:14]([C:17]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:18]=3[CH:19]=[N:20][N:21]4[CH3:26])=[CH:15][N:16]=[C:11]2[N:10](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[ClH:46]>O1CCOCC1>[ClH:46].[C:1]([NH:5][C:6]([C:8]1[C:12]2=[N:13][C:14]([C:17]3[CH:25]=[CH:24][CH:23]=[C:22]4[C:18]=3[CH:19]=[N:20][N:21]4[CH3:26])=[CH:15][N:16]=[C:11]2[NH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 71280233HCID 71280233, compound

Product 1

HCID 71280320HCID 71280320, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of N-tert-butyl-2-(1-methyl-1H-indazol-4-yl)-5-trityl-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide (154 mg, 0.261 mmol) in dioxane (20 mL) was bubbled HCl gas until saturation and then stirred at room temperature for 4 hours. Reaction mixture was concentrated and the residue was triturated with methanol (1 mL) then decanted and dried to afford N-tert-butyl-2-(1-methyl-1H-indazol-4-yl)-5H-pyrrolo[3,2-b]pyrazine-7-carboxamide hydrochloride (38 mg, 38%) as a white solid. LCMS: (M+H)+=349; 1H NMR (300 MHz, CDCl3): δ 9.77 (s, 1H), 8.89 (s, 1H), 8.54 (s, 1H), 8.39 (s, 2H), 7.66-7.52 (m, 3H), 4.20 (s, 3H), 1.58 (s, 9H).

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-7dff89950f984a2281fd88e7e46fc615
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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