4-Methylmorpholine → N-(2-Amino-Pyrimidin-5-yl)-2-Chloro-5-(3-Trifluoromethyl-Benzoylamino)-Benzamide

HRID 1662834

Reaction equation

HRID 1662834 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([Cl:18])=[C:13]([CH:17]=1)[C:14](O)=[O:15])=[O:7].CN1CCOCC1.[NH2:31][C:32]1[N:37]=[CH:36][C:35]([NH2:38])=[CH:34][N:33]=1>C(Cl)Cl>[NH2:31][C:32]1[N:37]=[CH:36][C:35]([NH:38][C:14](=[O:15])[C:13]2[CH:17]=[C:9]([NH:8][C:6](=[O:7])[C:5]3[CH:19]=[CH:20][CH:21]=[C:3]([C:2]([F:22])([F:23])[F:1])[CH:4]=3)[CH:10]=[CH:11][C:12]=2[Cl:18])=[CH:34][N:33]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 229075Pyrimidine-2,5-diamineHCID 534011722-Chloro-5-(3-(trifluoromethyl)benzamido)benzoic acid

Product 1

HCID 24962185N-(2-Amino-Pyrimidin-5-yl)-2-Chloro-5-(3-Trifluoromethyl-Benzoylamino)-BenzamideYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of intermediate 1 (Example 2) (380 mg, 1.11 mmol) in DCM was charged with CDMT (233 mg, 1.33 mmol), and NMM (0.3 mL, 2.73 mmol). After 1 hr of stirring, 2,5-diaminopyrimidine (121 mg, 1.10 mmol) was added and the solution was allowed to stir for 48 h. The mixture was concentrated and purified by HPLC to afford the title compound as a white solid (350 mg, 73%).

Workup

  1. stirringto stir for 48 h
  2. concentrationThe mixture was concentrated
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-22c9db19a4fe4ff899c5f9e817647a15
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Linked notes

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