Methanol → HCID 136250331, compound

HRID 706787Notes

Reaction equation

HRID 706787 reaction equation
[Na].[C:2]([C:5]1[N:6]([NH:10][C:11]([C:13]2[CH:21]=[CH:20][C:16]([C:17]([O-:19])=[O:18])=[CH:15][CH:14]=2)=O)[CH:7]=[CH:8][CH:9]=1)(=[O:4])[NH2:3].[CH3:22]O>>[CH3:22][O:19][C:17](=[O:18])[C:16]1[CH:20]=[CH:21][C:13]([C:11]2[NH:3][C:2](=[O:4])[C:5]3=[CH:9][CH:8]=[CH:7][N:6]3[N:10]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 5360545SodiumHCID 131733703HCID 131733703, compound

Product 1

HCID 136250331HCID 136250331, compound

Procedure

Sodium (65.3 mg, 2.84 mmol) is dissolved in methanol (5.0 ml). Then 4-[(2-carbamoylpyrrol-1-yl)carbamoyl]benzoate (544 mg, 1.90 mmol) is added. The mixture is irradiated in a microwave reactor at 150° C. for 1 hour. The solvent is evaporated and the residue is triturated with water. The solid is filtered off and washed with water. The residue is chromatographed on a silica gel column with methanol/dichloromethane as eluent to give 4-(4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-benzoic acid methyl ester as white fluffy solid; HPLC/MS 1.72 min (C), [M+H] 270;

Workup

  1. customThe mixture is irradiated in a microwave reactor at 150° C. for 1 hour
  2. customThe solvent is evaporated
  3. customthe residue is triturated with water
  4. filtrationThe solid is filtered off
  5. washwashed with water
  6. customThe residue is chromatographed on a silica gel column with methanol/dichloromethane as eluent

Sources & evidence

ORD record
ord-df71d00ca91e485284664c1bb276406e
Source dataset
uspto-grants-2015_11
Patent number
US09174995B2

Reaction notes

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