Acetic Acid → HCID 86631139, compound

HRID 912705Notes

Reaction equation

HRID 912705 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([CH:12]=O)[CH:7]=1)[CH2:2][CH2:3][CH3:4].N[C:15]1[NH:19][CH:18]=[N:17][C:16]=1[C:20]([NH2:22])=[O:21].C(O)(=O)C.C([BH3-])#[N:28].[Na+]>C(OCC)(=O)C.O>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][N:9]=[C:8]([CH2:12][NH:28][N:17]2[C:16]([C:20]([NH2:22])=[O:21])=[CH:15][N:19]=[CH:18]2)[CH:7]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 96795-Aminoimidazole-4-carboxamideHCID 5003444Sodium cyanoborohydrideHCID 86631138HCID 86631138, compound

Product 1

HCID 86631139HCID 86631139, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

The title compound was prepared in accordance with the general method described in Example 17(e) using 4-butoxypyridine-2-carbaldehyde (0.67 g, 5.0 mmol, obtained from Example 18(d)), 5-aminoimidazole-4-carboxamide (0.81 g, 4.5 mmol), acetic acid (0.58 mL, 9.0 mmol) and sodium cyanoborohydride (0.57 g, 9.0 mmol) with the exception for the following change in work-up. The crude product was dissolved in ethyl acetate/water (1:1, 60 mL). The pH was adjusted to 8. The aqueous layer was separated and extracted with ethyl acetate (2×20 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo to give the title compound (1.20 g, 90% yield). MS (ESI) m/z 290 (M+1).

Workup

  1. customThe title compound was prepared in accordance with the general method
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate (2×20 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-260eee7520f6453badcf73011a63112e
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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