Water → 7-Methoxy-4-(5-(3-thiazol-2-ylureido)thiophen-2-ylsulfanyl)quinoline-6-carboxamide

HRID 387852Notes

Reaction equation

HRID 387852 reaction equation
[NH2:1][C:2]1[S:6][C:5]([S:7][C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:21][CH3:22])=[C:15]([C:18]([NH2:20])=[O:19])[CH:16]=3)[N:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C1([O:29][C:30](=O)[NH:31][C:32]2[S:33][CH:34]=[CH:35][N:36]=2)C=CC=CC=1.C(OCC)(=O)C.O>CS(C)=O.CO>[CH3:22][O:21][C:14]1[CH:13]=[C:12]2[C:17]([C:8]([S:7][C:5]3[S:6][C:2]([NH:1][C:30]([NH:31][C:32]4[S:33][CH:34]=[CH:35][N:36]=4)=[O:29])=[CH:3][CH:4]=3)=[CH:9][CH:10]=[N:11]2)=[CH:16][C:15]=1[C:18]([NH2:20])=[O:19]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl Acetate2×HCID 651148phenyl N-(1,3-thiazol-2-yl)carbamateHCID 229362694-(5-Aminothiophen-2-ylsulfanyl)-7-methoxyquinoline-6-carboxamide

Product 1

HCID 229368697-Methoxy-4-(5-(3-thiazol-2-ylureido)thiophen-2-ylsulfanyl)quinoline-6-carboxamideYield 38.5%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

4-(5-Aminothiophen-2-ylsulfanyl)-7-methoxyquinoline-6-carboxamide (66.0 mg, 0.200 mmol) and thiazol-2-ylcarbamic acid phenyl ester (66.0 mg, 0.300 mmol) were stirred in dimethylsulfoxide (1 ml) at 85° C. for 2 hours. The reaction solution was distributed between ethyl acetate and water, the organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (eluent-ethyl acetate:methanol=15:1), and the fraction containing the target substance was concentrated, suspended in ethyl acetate and diluted with hexane, after which the crystals were filtered out, washed with hexane and then blow-dried to obtain the title compound (35.0 mg, 0.077 mmol, 38%) as colorless crystals.

Workup

  1. washthe organic layer was washed with water and saturated saline
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationthe drying agent was filtered off
  4. distillationthe filtrate was distilled off under reduced pressure
  5. customThe obtained crude product
  6. additionthe fraction containing the target substance
  7. concentrationwas concentrated
  8. additiondiluted with hexane
  9. filtrationafter which the crystals were filtered out
  10. washwashed with hexane
  11. customblow-dried

Sources & evidence

ORD record
ord-e3c9386252ae4be88c455ca8d33d029b
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

Loading…