Ammonia methanol → 3-{3-[4-(2,3,6-Trifluorobenzylsulfamoyl)-phenyl]-ureido}-benzamidine

HRID 497317Notes

Reaction equation

HRID 497317 reaction equation
CO[C:3](=[NH:34])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([S:20](=[O:33])(=[O:32])[NH:21][CH2:22][C:23]3[C:28]([F:29])=[CH:27][CH:26]=[C:25]([F:30])[C:24]=3[F:31])=[CH:16][CH:15]=2)=[O:12])[CH:5]=1.[NH3:35].CO>>[F:31][C:24]1[C:25]([F:30])=[CH:26][CH:27]=[C:28]([F:29])[C:23]=1[CH2:22][NH:21][S:20]([C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:11](=[O:12])[NH:10][C:6]2[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=2)[C:3]([NH2:35])=[NH:34])=[CH:15][CH:16]=1)(=[O:32])=[O:33]

Participants

3

Reactant 2

HCID 21705897Ammonia methanol2×HCID 697315573-{3-[4-(2,3,6-Trifluorobenzylsulfamoyl)-phenyl]-ureido}-benzimidic acid methyl ester

Product 1

HCID 100052473-{3-[4-(2,3,6-Trifluorobenzylsulfamoyl)-phenyl]-ureido}-benzamidine

Procedure

3-{3-[4-(2,3,6-Trifluorobenzylsulfamoyl)-phenyl]-ureido}-benzimidic acid methyl ester (250 mg, 0.5 mmol) was dissolved in NH3/MeOH (15 ml, 7 M). The solution was stirred overnight at rt. Further 10 ml of NH3/MeOH (7 M) were added and the mixture stirred for 3 h at 65° C. The solvents were evaporated and the solid residue purified by flash chromatography on silica gel with a gradient of AcOEt and MeOH. The fractions with the desired product were collected, evaporated and the product crystallized from MeOH/Et2O. Yield 50%.

Workup

  1. stirringthe mixture stirred for 3 h at 65° C
  2. customThe solvents were evaporated
  3. customthe solid residue purified by flash chromatography on silica gel with a gradient of AcOEt and MeOH
  4. customThe fractions with the desired product were collected
  5. customevaporated
  6. customthe product crystallized from MeOH/Et2O

Sources & evidence

ORD record
ord-096e54e1015e468daa36629bfb658adc
Source dataset
uspto-grants-2005_09
Patent number
US06949567B2

Reaction notes

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