Morpholine → HCID 90370196, compound

HRID 2176051Notes

Reaction equation

HRID 2176051 reaction equation
[Cl:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:32]=[CH:33][CH:34]=1)[C:6]([NH:8][C:9]1[S:10][C:11]2[CH2:31][CH2:30][CH2:29][CH2:28][C:12]=2[C:13]=1[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])=[CH:19][CH:18]=1)=[O:15])=[O:7].[NH:35]1[CH2:40][CH2:39][O:38][CH2:37][CH2:36]1>CN(C=O)C>[ClH:1].[ClH:1].[CH2:24]([N:23]([CH2:26][CH3:27])[C:20]1[CH:19]=[CH:18][C:17]([NH:16][C:14]([C:13]2[C:12]3[CH2:28][CH2:29][CH2:30][CH2:31][C:11]=3[S:10][C:9]=2[NH:8][C:6](=[O:7])[C:5]2[CH:32]=[CH:33][CH:34]=[C:3]([CH2:2][N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)[CH:4]=2)=[O:15])=[CH:22][CH:21]=1)[CH3:25]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 90370188HCID 90370188, compound

Product 1

HCID 90370196HCID 90370196, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 200 mg of 2-{[3-(chloromethyl)benzoyl]amino}-N-[4-(diethylamino)phenyl]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide and 8 mL of DMF was added 1.0 mL of morpholine, followed by stirring for 3 days at room temperature. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia solution=50:1:0.1). The obtained residue was dissolved in a mixed solution of ethyl acetate and ethanol (4:1), and 1.0 mL of 4.0 M hydrogen chloride/ethyl acetate solution was further added thereto. The precipitated solid was collected by filtration, thereby obtaining 183 mg of N-[4-(diethylamino)phenyl]-2-{[3-(morpholin-4-ylmethyl)benzoyl]amino}-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxamide dihydrochloride.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia solution=50:1:0.1)
  3. dissolutionThe obtained residue was dissolved in a mixed solution of ethyl acetate and ethanol (4:1), and 1.0 mL of 4.0 M hydrogen chloride/ethyl acetate solution
  4. additionwas further added
  5. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-c6f263f281f84f8cbed0b20a3db8794f
Source dataset
uspto-grants-2015_06
Patent number
US09062032B2

Reaction notes

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