Pyridine → HCID 23069568, compound

HRID 387979Notes

Reaction equation

HRID 387979 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[CH:10][CH:9]=[C:8]2[O:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([NH2:25])[CH:19]=1)=[O:4].[N:26]1[CH:31]=C[CH:29]=[CH:28][CH:27]=1.ClC(OC1C=CC=CC=1)=[O:34].C1(N)CC1>CN(C)C=O.O.C(OCC)(=O)C>[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[N:11]=[CH:10][CH:9]=[C:8]2[O:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([NH:25][C:31]([NH:26][CH:27]2[CH2:29][CH2:28]2)=[O:34])[CH:19]=1)=[O:4]

Participants

8

Reactant 4

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 69828CyclopropylamineHCID 22936471HCID 22936471, compound

Product 1

HCID 23069568HCID 23069568, compoundYield 74.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

After dissolving N6-methyl-4-(3-amino-4-chlorophenoxy)-7-methoxy-6-quinolinecarboxamide (179 mg, 0.50 mmol) in dimethylformamide (2 ml) under a nitrogen atmosphere, pyridine (0.061 ml, 0.75 mmol) and phenyl chloroformate (0.094 ml, 0.75 mmol) were added dropwise at room temperature and the mixture was stirred for 1 hour. Cyclopropylamine (0.2 ml) was added dropwise and the mixture was further stirred overnight. The reaction solution was distributed between ethyl acetate and water, washed with saturated saline and dried over anhydrous sodium sulfate. After distilling off the solvent, the crystals precipitated from ethyl acetate were filtered out and blow-dried to obtain the title compound (163.9 mg, 0.372 mmol, 74.3%) as white crystals.

Workup

  1. waitthe mixture was further stirred overnight
  2. washwashed with saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationAfter distilling off the solvent
  5. customthe crystals precipitated from ethyl acetate
  6. filtrationwere filtered out and
  7. customblow-dried

Sources & evidence

ORD record
ord-89cfb865ca0d4e53950bc2224fffba04
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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