Cyanamide → HCID 178486811, compound

HRID 1857230Notes

Reaction equation

HRID 1857230 reaction equation
[F: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>[F: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 22132660HCID 22132660, compound

Product 1

HCID 178486811HCID 178486811, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-(2-Fluorophenyl)-N'-(4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}thiourea (42 mg) obtained in Example 167, dicyclohexylcarbodiimide (37 mg) and a catalytic amount of diisopropylethyl amine were dissolved in methylene chloride (10 ml). To this solution, a solution of cyanamide (20 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 41 mg of the title compound (yield: 99%).

Workup

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

Sources & evidence

ORD record
ord-e2bcf8d2ef3d4d9380c8ae88453bf110
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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