Potassium Hydroxide → HCID 136592797, compound

HRID 57729Notes

Reaction equation

HRID 57729 reaction equation
[CH2:1]([O:8][CH:9]([CH3:21])[C:10]([NH:12][N:13]1[C:17]([C:18]([NH2:20])=[O:19])=[CH:16][N:15]=[CH:14]1)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>CCO.O>[CH2:1]([O:8][CH:9]([C:10]1[NH:20][C:18](=[O:19])[C:17]2=[CH:16][N:15]=[CH:14][N:13]2[N:12]=1)[CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 897172583-(2-Benzyloxy-propionylamino)-3H-imidazole-4-carboxylic acid amide

Product 1

HCID 136592797HCID 136592797, compoundYield 75.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of compound 10 (1.5 g, 5.2 mmol) in EtOH (10 mL) was added a solution of KOH (870 mg, 15.6 mmol) in H2O (4 mL). Then the resulting mixture was heated at 100° C. under microwave heating for one hour. After removal of the solvent, the mixture was poured into ice water and pH was adjusted to 7 with 1M aqueous HCl solution. The suspension was filtered and the solid was dried to give compound 11 (1.06 g, 75% yield) as a white solid. LC-MS: m/z 271 [M+H]+. 1H NMR (400 MHz, CDCl3): δ 8.70 (br. s, 1H), 8.10 (s, 1H), 7.92 (s, 1H), 7.39˜7.32 (m, 5H), 4.60 (m, 2H), 4.46 (q, J=6.4 Hz, 1H), 1.57 (d, J=6.4 Hz, 3H).

Workup

  1. temperatureheating for one hour
  2. customAfter removal of the solvent
  3. additionthe mixture was poured into ice water and pH
  4. filtrationThe suspension was filtered
  5. customthe solid was dried

Sources & evidence

ORD record
ord-8e3ea0a2e10a42adab85b0ecbe43ada7
Source dataset
uspto-grants-2016_09
Patent number
US09434733B2

Reaction notes

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