Cyanamide → HCID 178486812, compound

HRID 1857232Notes

Reaction equation

HRID 1857232 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[C:28]4[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=4)[N:22]=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)=S)[CH:5]=[CH:6][CH:7]=1.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:3]=[C:4]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][C:19]3[C:28]4[C:23](=[CH:24][C:25]([O:31][CH3:32])=[C:26]([O:29][CH3:30])[CH:27]=4)[N:22]=[CH:21][CH:20]=3)=[CH:14][CH:13]=2)=[N:41][C:40]#[N:39])[CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 9864CyanamideHCID 10868DicyclohexylcarbodiimideHCID 81531DiisopropylethylamineHCID 22132693HCID 22132693, compound

Product 1

HCID 178486812HCID 178486812, compoundYield 103.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-(3-Methylphenyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}thiourea (18 mg) obtained in Example 171, dicyclohexylcarbodiimide (35 mg) and a catalytic amount of diisopropylethyl amine were dissolved in methylene chloride (6 ml), to which a solution of cyanamide (23 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 19 mg of the title compound (yield: 95%).

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-81f946f964e842d781124fe6c9d8a1d3
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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