5-Aminoimidazole-4-carboxamide hydrochloride → HCID 86631113, compound

HRID 912659Notes

Reaction equation

HRID 912659 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)[N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:16]=[C:15]2[CH:28]=O.[BH3-]C#N.[Na+]>CO>[NH2:10][C:8]([C:7]1[NH:6][CH:5]=[N:4][C:3]=1[NH:2][CH2:28][C:15]1[C:14]2[C:18](=[CH:19][CH:20]=[C:12]([F:11])[CH:13]=2)[N:17]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:16]=1)=[O:9]

Participants

5

Reactant 3

HCID 661465-Aminoimidazole-4-carboxamide hydrochlorideHCID 5003444Sodium cyanoborohydrideHCID 86631112HCID 86631112, compound

Product 1

HCID 86631113HCID 86631113, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A reaction mixture of 4-amino-5-imidazolecarboxamide hydrochloride (0.20 g, 1.23 mmol), tert-butyl 5-fluoro-3-formyl-1H-indole-1-carboxylate (0.39 g, 1.48 mmol, obtained from Example 6(a)), and NaCNBH3 (0.078 g, 1.23 mmol) in methanol (3 mL) was stirred at r.t. for 1 h. Additional 5-fluoro-3-formyl-indole-1-carbonylic acid tert-butyl ester (0.31 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 (heptane/ethyl acetate (1:0 to 0:1) then CH2Cl2), obtaining 0.32 g (70%) of the title compound. MS (ESI) m/z 374 (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 (heptane/ethyl acetate (1:0 to 0:1)

Sources & evidence

ORD record
ord-9631e7e6519e47ee889c44a6532529cb
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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