Benzenamine, 2-chloro-5-(trifluoromethyl)- → HCID 24997947, compound

HRID 659024Notes

Reaction equation

HRID 659024 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)([N:3]1[CH:7]=[CH:6]N=C1)=[O:2].[Cl:13][C:14]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=CC=1N.NC1C=[CH:46][C:29]([O:30][C:31]2[CH:36]=[CH:35][N:34]=[C:33]([NH:37][CH2:38][CH2:39][CH2:40][O:41][Si](C)(C)C)[N:32]=2)=[CH:28][CH:27]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl.C1COCC1>[Cl:13][C:14]1[CH:20]=[CH:19][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:11][C:12]=1[NH:8][C:1]([NH:3][C:7]1[CH:6]=[CH:46][C:29]([O:30][C:31]2[CH:36]=[CH:35][N:34]=[C:33]([NH:37][CH2:38][CH2:39][CH2:40][OH:41])[N:32]=2)=[CH:28][CH:27]=1)=[O:2]

Participants

7

Reactant 4

HCID 8475Benzenamine, 2-chloro-5-(trifluoromethyl)-HCID 682631,1'-CarbonyldiimidazoleHCID 2724141Tetrabutylammonium FluorideHCID 67523859HCID 67523859, compound

Product 1

HCID 24997947HCID 24997947, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

105 mg (0.65 mmol) 1,1′-Carbonyl-diimidazol (CDI) was given to a solution of 115 mg (0.59 mmol) 2-chloro-5-(trifluoromethyl)aniline in 4.0 ml dichloromethane. After stirring for 12 h at r.t. a solution of 220 mg (0.59 mmol) [4-(4-Amino-phenoxy)-pyrimidin-2-yl]-(3-trimethylsilanyloxy-propyl)-amine in 6 ml dichloromethane within 30 min. was added and the mixture stirred for 5 d at r.t. A solution of 1.4 ml (1.4 mmol) 1 M tetrabutylammonium fluoride in THF was given to the mixture and stirring continued for 12 h. The reaction mixture was evaporated and the residue was purified by chromatography on silica gel (dichloromethane/ethanol 96:4). Yield: 6 mg (2%) of the title compound.

Workup

  1. additionwas added
  2. stirringstirring
  3. waitcontinued for 12 h
  4. customThe reaction mixture was evaporated
  5. customthe residue was purified by chromatography on silica gel (dichloromethane/ethanol 96:4)

Sources & evidence

ORD record
ord-461f0dd182df4830a4ed9e4177126750
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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