5-Aminoimidazole-4-carboxamide hydrochloride → HCID 67415544, compound

HRID 912658Notes

Reaction equation

HRID 912658 reaction equation
Cl.[NH2:2][C:3]1[N:4]=[CH:5][NH:6][C:7]=1[C:8]([NH2:10])=[O:9].[F:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](C=O)=[CH:15]2.[BH3-]C#[N:25].[Na+]>CO>[F:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16]([NH:25][NH:2][C:3]1[N:4]=[CH:5][NH:6][C:7]=1[C:8]([NH2:10])=[O:9])=[CH:15]2

Participants

5

Reactant 3

HCID 661465-Aminoimidazole-4-carboxamide hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 189681295-Fluoro-1H-indole-2-carbaldehyde2×

Product 1

HCID 67415544HCID 67415544, compoundYield 111.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A reaction mixture of 4-amino-5-imidazolecarboxamide hydrochloride (0.48 g, 2.94 mmol), 5-fluoro-1H-indole-2-carbaldehyde (0.40 g, 2.45 mmol), and NaCNBH3 (0.15 g, 2.45 mmol) in methanol (3 mL) was stirred at r.t. for 1 h. Additional 5-fluoro-1H-indole-2-carbaldehyde (0.42 equiv.) was added and after stirring at r.t. for 1 h the mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with water. The aqueous phase was extracted twice with ethyl acetate. The combined organic layers were dried (MgSO4) and concentrated. The crude product was purified by flash column chromatography (CH2Cl2/methanol gradient; 0 to 20% methanol), obtaining 0.75 g (70%) of the title compound. MS (ESI) m/z 272 (M−1).

Workup

  1. stirringafter stirring at r.t. for 1 h the mixture
  2. concentrationwas concentrated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. extractionThe aqueous phase was extracted twice with ethyl acetate
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. concentrationconcentrated
  8. customThe crude product was purified by flash column chromatography (CH2Cl2/methanol gradient; 0 to 20% methanol)

Sources & evidence

ORD record
ord-02fa198a60b346c29345c4faac845a61
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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