Water → 5-Chloro-N-(3-{[3-fluoro-4-(3-oxo-4-morpholinyl)phenyl]amino}-2-hydroxypropyl)-2-thiophenecarboxamide

HRID 499736Notes

Reaction equation

HRID 499736 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][C:9]2=[O:14])=[C:4]([F:15])[CH:3]=1.[Cl:16][C:17]1[S:21][C:20]([C:22]([NH:24][CH2:25][CH:26]2[CH2:28][O:27]2)=[O:23])=[CH:19][CH:18]=1.O>C(O)C>[Cl:16][C:17]1[S:21][C:20]([C:22]([NH:24][CH2:25][CH:26]([OH:27])[CH2:28][NH:1][C:2]2[CH:7]=[CH:6][C:5]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][C:9]3=[O:14])=[C:4]([F:15])[CH:3]=2)=[O:23])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 962WaterHCID 219197985-chloro-N-(2-oxiranylmethyl)-2-thiophenecarboxamideHCID 231053114-(4-Amino-2-fluoro-phenyl)-morpholin-3-one

Product 1

HCID 210707105-Chloro-N-(3-{[3-fluoro-4-(3-oxo-4-morpholinyl)phenyl]amino}-2-hydroxypropyl)-2-thiophenecarboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

800 mg (3.8 mmol) of 4-(4-amino-2-fluorophenyl)-3-morpholinone and 700 mg (3.22 mmol) of 5-chloro-N-(2-oxiranylmethyl)-2-thiophenecarboxamide are heated in 15 ml of ethanol and 1 ml of water under reflux for 6 hours. The mixture is evaporated in vacuo, the crystals which have separated out after treatment with ethyl acetate are filtered off with suction, and chromatography of the mother liquor results in 276 mg (17% of theory) of the target compound.

Workup

  1. customThe mixture is evaporated in vacuo
  2. customthe crystals which have separated out after treatment with ethyl acetate
  3. filtrationare filtered off with suction, and chromatography of the mother liquor
  4. customresults in 276 mg (17% of theory) of the target compound

Sources & evidence

ORD record
ord-23c0b1ef7eef4a439f61e36f51cb7ac1
Source dataset
uspto-grants-2010_08
Patent number
US07767702B2

Reaction notes

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