Dimethylformamide → HCID 22048197, compound

HRID 1830841Notes

Reaction equation

HRID 1830841 reaction equation
[Cl:1][C:2]1[C:3]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)=[C:4]2[C:18]3[CH2:19][CH2:20][CH:21]([C:23](O)=[O:24])[CH2:22][C:17]=3[S:16][C:5]2=[N:6][C:7]=1[CH2:8][N:9]1[C:13](=[O:14])[CH2:12][CH2:11][C:10]1=[O:15].[NH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1.Cl.CN(C)CCCN=C=NCC.CN(C=O)C>O>[Cl:1][C:2]1[C:3]([C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)=[C:4]2[C:18]3[CH2:19][CH2:20][CH:21]([C:23]([N:34]4[CH2:39][CH2:38][O:37][CH2:36][CH2:35]4)=[O:24])[CH2:22][C:17]=3[S:16][C:5]2=[N:6][C:7]=1[CH2:8][N:9]1[C:13](=[O:14])[CH2:12][CH2:11][C:10]1=[O:15]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8083MorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22048186HCID 22048186, compound

Product 1

HCID 22048197HCID 22048197, compoundYield 455.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of the compound obtained in Example 37 (500 mg), morpholine (99 mg), N,N-dimethylaminopyridine (13 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (197 mg), and DMF (10 ml) was stirred at room temperature for 10 hours. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and then evaporated under reduced pressure to remove the solvent. The residue was subjected to column chromatography on silica gel to obtain 1-{[3-chloro-4-(4-methoxyphenyl)-7-[(4-morpholinyl)carbonyl]-5,6,7,8-tetrahydro[1]benzothieno[2,3-b]pyridin-2-yl]methyl}-2,5-pyrrolidinedione (2.6 g, 92%) from the eluates with ethyl acetate. It was recrystallized from chloroform-hexane. Colorless prisms. Melting point 170–171° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. customto remove the solvent

Sources & evidence

ORD record
ord-d929f3ab91d447acb439900af3ee9675
Source dataset
uspto-grants-2006_06
Patent number
US07067527B2

Reaction notes

Loading…