4-Chloro-3-(trifluoromethyl)aniline → HCID 58902315, compound

HRID 1640169Notes

Reaction equation

HRID 1640169 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([O:15][C:16]2[CH:25]=[C:24]3[C:19]([CH:20]=[CH:21][C:22]([C:26](O)=[O:27])=[CH:23]3)=[CH:18][CH:17]=2)[CH:12]=[CH:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:29][C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[CH:32][C:31]=1[C:37]([F:40])([F:39])[F:38].CCN=C=NCCCN(C)C.Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[Cl:29][C:30]1[CH:36]=[CH:35][C:33]([NH:34][C:26]([C:22]2[CH:23]=[C:24]3[C:19]([CH:18]=[CH:17][C:16]([O:15][C:13]4[CH:12]=[CH:11][N:10]=[C:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH:14]=4)=[CH:25]3)=[CH:20][CH:21]=2)=[O:27])=[CH:32][C:31]=1[C:37]([F:38])([F:39])[F:40]

Participants

7

Reactant 3

HCID 675744-Chloro-3-(trifluoromethyl)anilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58902355HCID 58902355, compound

Product 1

HCID 58902315HCID 58902315, compoundYield 81.8%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-({2-[(tert-butoxycarbonyl)amino]pyridin-4-yl}oxy)-2-naphthoic acid (350 mg, 0.92 mmol) in DCM (9.0 mL), was added 4-chloro-3-(trifluoromethyl)aniline (198.0 mg, 1.0 mmol); EDCl (194 mg, 1.0 mmol) and DMAP (124 mg, 1.0 mmol). The mixture was allowed to stir for 18 h then diluted with EtOAc and washed with water and then brine. The organic phase was dried (Na2SO4) and evaporated, and the residue was triturated with DCM/EtOAc/MeOH to yield the title compound as a white solid (420 mg, 81.8%). LCMS: (FA) ES+ 558.1, ES− 556.1.

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. customevaporated
  4. customthe residue was triturated with DCM/EtOAc/MeOH

Sources & evidence

ORD record
ord-9967249763eb4d75a16f01d3d79a226a
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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