Cyanamide → HCID 178486810, compound

HRID 1857231Notes

Reaction equation

HRID 1857231 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:28]3[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=3)[N:22]=[CH:21][CH:20]=2)=[CH:14][CH:13]=1)=S.C1([N:39]=[C:40]=[N:41]C2CCCCC2)CCCCC1.C(N(C(C)C)CC)(C)C.N#CN>C(Cl)Cl.C1COCC1>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:28]3[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=3)[N:22]=[CH:21][CH:20]=2)=[CH:14][CH:13]=1)=[N:41][C:40]#[N:39]

Participants

7

Reactant 4

HCID 9864CyanamideHCID 10868DicyclohexylcarbodiimideHCID 81531DiisopropylethylamineHCID 22132681HCID 22132681, compound

Product 1

HCID 178486810HCID 178486810, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-(2-Methylphenyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}thiourea (24 mg) obtained in Example 170, dicyclohexylcarbodiimide (45 mg) and a catalytic amount of diisopropylethyl amine were dissolved in methylene chloride (7 ml), to which a solution of cyanamide (28 mg) in THF (1 ml) was added, and the admixture was stirred at room temperature overnight. After removing the solvent by distillation, the resulting residue was purified by column chromatography on silica gel eluting with chloroform/methanol (100/1) to obtain 18 mg of the title compound (yield: 76%).

Workup

  1. additionwas added
  2. customAfter removing the solvent
  3. distillationby distillation
  4. customthe resulting residue was purified by column chromatography on silica gel eluting with chloroform/methanol (100/1)

Sources & evidence

ORD record
ord-58bab4b41ac2488cafaf460256566379
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

Loading…