Dicyclohexylcarbodiimide → (1H-Benzoimidazol-2-yl)-[4-(4-chloro-5-methylsulfanyl-6-morpholin-4-yl-pyrimidin-2-yl)-phenyl]-amine

HRID 629015Notes

Reaction equation

HRID 629015 reaction equation
[NH2:1][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]([C:18]2[N:23]=[C:22]([Cl:24])[C:21]([S:25][CH3:26])=[C:20]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[N:19]=2)=[CH:14][CH:13]=1)=S.C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[NH:1]1[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N:8]=[C:9]1[NH:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[N:23]=[C:22]([Cl:24])[C:21]([S:25][CH3:26])=[C:20]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)[N:19]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 866735031-(2-Amino-phenyl)-3-[4-(4-chloro-5-methylsulfanyl-6-morpholin-4-yl-pyrimidin-2-yl)-phenyl]-thiourea

Product 1

HCID 86673504(1H-Benzoimidazol-2-yl)-[4-(4-chloro-5-methylsulfanyl-6-morpholin-4-yl-pyrimidin-2-yl)-phenyl]-amineYield 62.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(2-amino-phenyl)-3-[4-(4-chloro-5-methylsulfanyl-6-morpholin-4-yl-pyrimidin-2-yl)-phenyl]-thiourea (120 mg, 1.0 eq.) and DCC (0.18 g, 0.271 mmol, 1.1 eq.) in THF (8 ml) was reacted for 9 hrs at 80-90° C. The resulting mixture was dried in vacuo, crystallized in EA solution, filtered to give a yellow solid (69.5 mg, 62.3%), which was then dried in vacuo to give a product.

Workup

  1. customwas reacted for 9 hrs at 80-90° C
  2. customThe resulting mixture was dried in vacuo
  3. customcrystallized in EA solution
  4. filtrationfiltered

Sources & evidence

ORD record
ord-3b7c4505889843babb8bcd391aa275ae
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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