Tetrahydrofuran → HCID 117601062, compound

HRID 1773743Notes

Reaction equation

HRID 1773743 reaction equation
NC1C(NC)=[C:4]([CH:9]=[C:10]([C:12]2[C:13]([CH3:18])=[N:14][O:15][C:16]=2[CH3:17])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[C:21]([N:28]1[CH:32]=[CH:31][N:30]=[CH:29]1)(N1C=CN=C1)=O.[O:33]1CCCC1>>[CH3:18][C:13]1[C:12]([C:10]2[CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[C:32]3[N:28]([CH3:21])[C:29](=[O:33])[NH:30][C:31]=3[CH:11]=2)=[C:16]([CH3:17])[O:15][N:14]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 117601845HCID 117601845, compound

Product 1

HCID 117601062HCID 117601062, compoundYield 35%

Conditions

Temperature
100 °C

Procedure

Methyl 3-amino-5-(3,5-dimethylisoxazol-4-yl)-2-(methylamino)benzoate (1.1 g, 4 mmol) and 1,1′-carbonyldiimidazole (1.3 g, 7.99 mmol) were stirred in Tetrahydrofuran (100 ml) in a sealed pressure vessel. Reaction was heated to 100° C. and allowed to react overnight. Next day solvents were removed under reduced pressure. Material was slurried in minimal DCM, sonicated and filtered. Solids were air dried to afford methyl 6-(3,5-dimethylisoxazol-4-yl)-3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazole-4-carboxylate as an off-white powder (417 mg, 35%).

Workup

  1. customReaction
  2. customto react overnight
  3. customNext day solvents were removed under reduced pressure
  4. customsonicated
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-0a5d4c6c634444978a0251dcffd01eac
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

Loading…