Pyridine → HCID 22936754, compound

HRID 853420Notes

Reaction equation

HRID 853420 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-0f011357c7f0401cbc54c37321ea1cab
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

Loading…