Pyridine → HCID 22936754, compound

HRID 387899Notes

Reaction equation

HRID 387899 reaction equation
[NH2:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[C:14]([C:17]#[N:18])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:4][C:3]=1[Cl:29].[N:30]1[CH:35]=C[CH:33]=[CH:32][CH:31]=1.ClC(OC1C=CC=CC=1)=[O:38].C1(N)CC1>CN(C)C=O.C(OCC)C.O>[CH2:20]([O:19][C:13]1[CH:12]=[C:11]2[C:16]([C:7]([O:6][C:5]3[CH:27]=[CH:28][C:2]([NH:1][C:35]([NH:30][CH:31]4[CH2:33][CH2:32]4)=[O:38])=[C:3]([Cl:29])[CH:4]=3)=[CH:8][CH:9]=[N:10]2)=[CH:15][C:14]=1[C:17]#[N:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

8

Reactant 4

HCID 1049PyridineHCID 15891Phenyl chloroformateHCID 69828CyclopropylamineHCID 22936238HCID 22936238, compound

Product 1

HCID 22936754HCID 22936754, compoundYield 88.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

After dissolving 4-(4-amino-3-chlorophenoxy)-7-benzyloxy-6-cyanoquinoline (8.037 g, 20.0 mmol) in dimethylformamide (40 ml) under a nitrogen atmosphere, pyridine (1.94 ml, 24.0 mmol) and phenyl chloroformate (3.01 ml, 24.0 mmol) were added dropwise at room temperature and the mixture was stirred for 1 hour. Cyclopropylamine (3.46 ml, 50 mmol) was added dropwise, and the mixture was further stirred for 3 hours. Water (400 ml) and diethyl ether (400 ml) were added to the reaction solution, and after stirring overnight, the precipitated crystals were filtered out, washed with water and diethyl ether and dried at 70° C. to obtain the title compound (8.570 g, 17.7 mmol, 88.4%) as light brown crystals.

Workup

  1. stirringthe mixture was further stirred for 3 hours
  2. stirringafter stirring overnight
  3. filtrationthe precipitated crystals were filtered out
  4. washwashed with water and diethyl ether
  5. customdried at 70° C.

Sources & evidence

ORD record
ord-25bdd05f473e4bb784d63fefbe36afee
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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