Methanol → HCID 22649370, compound

HRID 393266Notes

Reaction equation

HRID 393266 reaction equation
[CH2:1]([O:5][C:6]1[C:7]([O:19][CH3:20])=[CH:8][CH:9]=[C:10]2[C:15]=1[NH:14][C:13](=[O:16])[C:12]([CH2:17][NH2:18])=[CH:11]2)[CH2:2][CH2:3][CH3:4].[F:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]=[C:29]=[O:30])=[CH:24][CH:23]=1.CO.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:1]([O:5][C:6]1[C:7]([O:19][CH3:20])=[CH:8][CH:9]=[C:10]2[C:15]=1[NH:14][C:13](=[O:16])[C:12]([CH2:17][NH:18][C:29]([NH:28][C:25]1[CH:26]=[CH:27][C:22]([F:21])=[CH:23][CH:24]=1)=[O:30])=[CH:11]2)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 709554-Fluorophenyl isocyanateHCID 22649354HCID 22649354, compound

Product 1

HCID 22649370HCID 22649370, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

8-Butoxy-3-aminomethyl-7-methoxy-2-oxo-1,2-dihydroquinoline (56.6 mg, 0.205 mmol) obtained in Example 7-2 was dissolved in chloroform (1 ml), and 4-fluorophenyl isocyanate (25.6 μl, 0.225 mmol) was successively added thereto while being cooled with ice. The mixture was stirred at the same temperature for 30 minutes, to which methanol (30 μl) and triethylamine (30 μl) were added, and was further stirred for 30 minutes. The reaction solution was concentrated under reduced pressure, and the resultant residue was washed with toluene to give the title compound (73 mg, yield 86%) as colorless crystals (Table 31).

Workup

  1. temperaturewhile being cooled with ice
  2. additionwere added
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. washthe resultant residue was washed with toluene

Sources & evidence

ORD record
ord-f222c4d982d04877b4ba0a48e9023d83
Source dataset
uspto-grants-2004_10
Patent number
US06806276B2

Reaction notes

Loading…