Acetic Acid → HCID 67415024, compound

HRID 912712Notes

Reaction equation

HRID 912712 reaction equation
[CH3:1][C:2]1[C:6]([CH:7]=O)=[C:5]([CH3:9])[O:4][N:3]=1.[NH2:10][C:11]1[NH:15][CH:14]=[N:13][C:12]=1[C:16]([NH2:18])=[O:17].C(O)(=O)C.C([BH3-])#N.[Na+]>>[CH3:1][C:2]1[C:6]([CH2:7][NH:10][C:11]2[N:15]=[CH:14][NH:13][C:12]=2[C:16]([NH2:18])=[O:17])=[C:5]([CH3:9])[O:4][N:3]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 96795-Aminoimidazole-4-carboxamideHCID 2895763,5-Dimethyl-4-IsoxazolecarbaldehydeHCID 5003444Sodium cyanoborohydride2×

Product 1

HCID 67415024HCID 67415024, compoundYield 97%

Procedure

The title compound was prepared in accordance with the general method described in Example 17(e) using 3,5-dimethylisoxazole-4-carbaldehyde (0.50 g, 4.0 mmol), 5-amino-imidazole-4-carboxamide (0.50 g, 4.0 mmol), acetic acid (0.23 mL, 4.0 mmol) and sodium cyanoborohydride (0.30 g, 4.8 mmol) with the exception that after stirring o.n., more sodium cyanoborohydride (0.04 g, 0.6 mmol) was added and the reaction mixture refluxed for 2 h. The reaction mixture was then concentrated in vacuo and the crude product was triturated with ethyl ether and the solid removed by filtration. The filtrate was concentrated to give the title compound (0.91 g, 97% yield). This material was used in the next step without further purification. MS (ESI) m/z 236 (M+1).

Workup

  1. customThe title compound was prepared in accordance with the general method
  2. temperaturethe reaction mixture refluxed for 2 h
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. customthe crude product was triturated with ethyl ether
  5. customthe solid removed by filtration
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-8412bbafabc14e1c95f4ac6f824f3873
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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