Cyanamide → HCID 178486813, compound

HRID 1857229Notes

Reaction equation

HRID 1857229 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([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:4][CH:3]=1.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][C:5]([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:4][CH:3]=1

Participants

7

Reactant 4

HCID 9864CyanamideHCID 10868DicyclohexylcarbodiimideHCID 81531DiisopropylethylamineHCID 11236257HCID 11236257, compound

Product 1

HCID 178486813HCID 178486813, compoundYield 101.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

N-(4-Fluorophenyl)-N'-(4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl)thiourea (33 mg) obtained in Example 165, dicyclohexylcarbodiimide (31 mg) and a catalytic amount of diisopropylethyl amine were dissolved in methylene chloride (10 ml). To this solution, a solution of cyanamide (16 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 34 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-fb67c4d0c2584a92812316f73de97f40
Source dataset
uspto-grants-2000_11
Patent number
US06143764

Reaction notes

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