Ethanol → 5-Chloro-N-((2R)-2-hydroxy-3-((4-(3-oxo-4-morpholinyl)phenyl)amino)propyl)-2-thiophenecarboxamide

HRID 425236Notes

Reaction equation

HRID 425236 reaction equation
Br[CH2:2][C@@H:3]([OH:14])[CH2:4][NH:5][C:6]([C:8]1[S:9][C:10]([Cl:13])=[CH:11][CH:12]=1)=[O:7].[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][C:23]2=[O:28])=[CH:18][CH:17]=1.N1C(C)=CC(C)=CC=1C.C(O)C>C1(C)C=CC=CC=1.C(O)CCC>[OH:14][C@H:3]([CH2:2][NH:15][C:16]1[CH:17]=[CH:18][C:19]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][C:23]2=[O:28])=[CH:20][CH:21]=1)[CH2:4][NH:5][C:6]([C:8]1[S:9][C:10]([Cl:13])=[CH:11][CH:12]=1)=[O:7]

Participants

7

Reactant 4

HCID 702EthanolHCID 79532,4,6-TrimethylpyridineHCID 10108741N-((S)-3-bromo-2-hydroxypropyl)-5-chlorothiophene-2-carboxamideHCID 111948544-(4-Aminophenyl)morpholin-3-one

Product 1

HCID 100015745-Chloro-N-((2R)-2-hydroxy-3-((4-(3-oxo-4-morpholinyl)phenyl)amino)propyl)-2-thiophenecarboxamide

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
104 °C

Procedure

55 g of N-((S)-3-bromo-2-hydroxypropyl)-5-chlorothiophene-2-carboxamide (IX) and 29.4 g of 4-(4-aminophenyl)-3-morpholinone (III) (a preparation method is described, for example, in WO-A 01/47919 on pages 55 to 57) are suspended at from 20 to 25° C. in 500 ml of toluene and admixed with 18.5 g of collidine and 10 ml of ethanol. The reaction mixture is heated to from 103 to 105° C. for 6 hours and then admixed while hot with 50 ml of 1-butanol. After cooling to 30° C., the precipitated reaction product is filtered off with suction, washed with toluene and water and dried.

Workup

  1. temperatureAfter cooling to 30° C.
  2. customthe precipitated reaction product
  3. filtrationis filtered off with suction
  4. washwashed with toluene and water
  5. customdried

Sources & evidence

ORD record
ord-420df85599a842b5b71a20aa13941504
Source dataset
uspto-grants-2012_01
Patent number
US08106192B2

Reaction notes

Loading…