HCID 19369813, compound → HCID 19369841, compound

HRID 849205Notes

Reaction equation

[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])[C:14]=3[N:13]=[C:12](Cl)[C:11]=2[CH:10]=[CH:9]1>NCCCCO>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:20]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])[C:14]=3[N:13]=[C:12]([NH:8][CH2:20][CH2:19][CH2:14][CH2:15][OH:21])[C:11]=2[CH:10]=[CH:9]1

Participants

Conditions

Temperature: 180 °C

Procedure

1-(2-Methylphenyl)-4-chloro-6-β,β,β-trifluoroethoxypyrrolo[3,2-c]quinoline(600 mg, 1.5 mmol), prepared by the procedures of Step 1 and Step 2 in the Example 34, was added in 4-amino-1-butanol(10 ml) in the pressure tube, and refluxed at 180° C. for 3 hours. After removing the excess 4-amino-butanol by distillation under reduced pressure, the residue was diluted in dichloromethane(20 ml), and washed with water(15 ml) for 3 times. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography to obtain 459 mg of desired compound as solid in 69% of yield.

Workup

customAfter removing the excess 4-amino-butanol
distillationby distillation under reduced pressure
additionthe residue was diluted in dichloromethane(20 ml)
washwashed with water(15 ml) for 3 times
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-9fa7e9143d024698804ad87d01cda134
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06011044

Reaction notes

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