Water → HCID 19791286, compound

HRID 1655246Notes

Reaction equation

HRID 1655246 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[C:9]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:10]([C:12]1[CH:17]=[CH:16][C:15]([N:18]2[C:26]3[CH:25]=[CH:24][N:23]=[CH:22][C:21]=3[N:20]=[C:19]2[CH3:27])=[CH:14][CH:13]=1)=O.S(O)(O)(=O)=O.[CH3:38][O:39][C:40](=[NH:42])[NH2:41].C(=O)(O)[O-].[Na+].O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[C:9]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([N:18]3[C:26]4[CH:25]=[CH:24][N:23]=[CH:22][C:21]=4[N:20]=[C:19]3[CH3:27])=[CH:14][CH:13]=2)[NH:42][C:40]([O:39][CH3:38])=[N:41]1

Participants

6

Reactant 4

HCID 962WaterHCID 169039Carbamimidic acid, methyl ester, sulfate (1:1)HCID 516892Sodium BicarbonateHCID 54284370HCID 54284370, compound

Product 1

HCID 19791286HCID 19791286, compoundYield 46.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(2-chlorophenyl)-2-ethoxycarbonyl-1-[4-(2-methylimidazo[4,5-c]pyrid-1-yl)phenyl]prop-2-ene-1-one (200 mg --see Preparation 1), O-methylisourea hydrogen sulphate (155 mg) and sodium bicarbonate (240 mg) was heated in dimethylformamide (DMF) (5 ml) at 70° C. for 16 hours. The cooled mixture was poured into water (25 ml) and extracted with ethyl acetate (3×25 ml). The combined organic phases were washed with water, dried (MGSO4), filtered and evaporated and the residue was chromatographed on silica eluting with methylene ebloride/metbanol. The fractions containing the product were combined and evaporated to give the title compound (105 mg), m.p. 228°-232° C.

Workup

  1. extractionextracted with ethyl acetate (3×25 ml)
  2. washThe combined organic phases were washed with water
  3. customdried (MGSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customthe residue was chromatographed on silica eluting with methylene ebloride/metbanol
  7. additionThe fractions containing the product
  8. customevaporated

Sources & evidence

ORD record
ord-34c50137ff9f44908a7a59cc6925228e
Source dataset
uspto-grants-1993_10
Patent number
US05250531

Reaction notes

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