Dimethylformamide → HCID 19841385, compound

HRID 622344Notes

Reaction equation

HRID 622344 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]3[C:14]4[CH2:15][NH:16][CH2:17][CH2:18][C:13]=4[NH:12][C:7]=3[CH:8]=[N:9]2)=[CH:4][CH:3]=1.Cl[CH2:20][CH2:21][CH2:22][C:23]1[C:27]2[CH:28]=[CH:29][C:30]([F:32])=[CH:31][C:26]=2[O:25][N:24]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]3[C:14]4[CH2:15][NH:16][CH2:17][CH:18]([CH2:20][CH2:21][CH2:22][C:23]5[C:27]6[CH:28]=[CH:29][C:30]([F:32])=[CH:31][C:26]=6[O:25][N:24]=5)[C:13]=4[NH:12][C:7]=3[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 109108803-(3-Chloropropyl)-6-fluorobenzo[d]isoxazoleHCID 19841388HCID 19841388, compound

Product 1

HCID 19841385HCID 19841385, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture prepared from 5.15 g of 3-chloro-7,8,9,10-tetrahydro-11H-pyrido[3',4':4,5]pyrrolo[2,3-c]quinoline, 7.0 g of 3-(3-chloropropyl)-6-fluorobenzisoxazole, 4.0 g of potassium carbonate (powdered) and 30 ml of N,N-dimethylformamide was stirred at 100° C. for 2 hours. The mixture was diluted with 150 ml of water and the oily precipitate was purified by high performance liquid chromatography (HPLC) using dichloromethane/methanol mixtures of 95:5 and 10:1 ratios. The clean fractions were combined and concentrated. The residue was stirred in isopropanol and filtered. The yield was 1.2 g, mp=221°-222° C.

Workup

  1. customthe oily precipitate was purified by high performance liquid chromatography (HPLC)
  2. concentrationconcentrated
  3. stirringThe residue was stirred in isopropanol
  4. filtrationfiltered

Sources & evidence

ORD record
ord-40365f2efd5f41e086a627aa05411b52
Source dataset
uspto-grants-1988_09
Patent number
US04771052

Reaction notes

Loading…