2-(Trifluoromethyl)aniline → 5-(4-Fluorophenyl)-2-methyl-1-(2-trifluoromethylphenyl)-1H-pyrrole-3-carboxylic acid (4-methanesulfonyl-phenyl) amide

HRID 383758Notes

Reaction equation

HRID 383758 reaction equation
C(O[C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[N:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[C:24]([F:27])([F:26])[F:25])[C:7]=1[CH3:28])=[O:5])C.FC(F)(F)C1C=CC=CC=1N.C(OC(=O)C(C(=O)C)CC(C1C=CC(F)=CC=1)=O)C.FC1C=CC(N)=CC=1.[CH3:67][S:68]([C:71]1[CH:76]=[CH:75][C:74]([NH:77]C(C2C=C(C3C=CC(F)=CC=3)N(C3C=CC(F)=CC=3)C=2C)=O)=[CH:73][CH:72]=1)(=[O:70])=[O:69].CS(C1C=CC(N)=CC=1)(=O)=O>>[CH3:67][S:68]([C:71]1[CH:76]=[CH:75][C:74]([NH:77][C:4]([C:6]2[CH:10]=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[N:8]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([F:27])([F:25])[F:26])[C:7]=2[CH3:28])=[O:5])=[CH:73][CH:72]=1)(=[O:69])=[O:70]

Participants

7

Reactant 6

HCID 69222-(Trifluoromethyl)anilineHCID 97314-FluoroanilineHCID 796174-(Methylsulfonyl)anilineHCID 115763441,5-bis-(4-fluorophenyl)-2-methyl-1H-pyrrole-3-carboxylic acid (4-methanesulfonyl-phenyl) amideHCID 141739732-Acetyl-4-(4-fluorophenyl)-4-oxobutyric acid ethyl esterHCID 672526905-(4-fluorophenyl)-2-methyl-1-(2-trifluoromethylphenyl)-1H-pyrrole-3-carboxylic acid ethyl ester

Product 1

HCID 598079645-(4-Fluorophenyl)-2-methyl-1-(2-trifluoromethylphenyl)-1H-pyrrole-3-carboxylic acid (4-methanesulfonyl-phenyl) amide

Procedure

In a manner similar to that described for Examples 16C-D, the title compound was prepared from 5-(4-fluorophenyl)-2-methyl-1-(2-trifluoromethylphenyl)-1H-pyrrole-3-carboxylic acid ethyl ester, which was synthesized from 2-trifluoromethyl-aniline and 2-acetyl-4-(4-fluorophenyl)-4-oxobutyric acid ethyl ester using the procedures described in WO 03/027069. 1H-NMR (CDCl3): δ 7.92-7.84 (5H, m), 7.77-7.69 (2H, m), 7.63-7.60 (1H, m), 7.42 (1H, d), 7.07-7.03 (2H, m), 6.88-6.84 (2H, m), 6.60 (1H, s), 3.05 (3H, s), 2.33 (3H, s). MS (ESI): 517 (MH+). B. In a manner similar to that described for Example 20A, but replacing 2-trifluoromethyl-aniline with 4-fluoroaniline, the following compound was prepared: 1,5-bis-(4-fluorophenyl)-2-methyl-1H-pyrrole-3-carboxylic acid (4-methanesulfonyl-phenyl) amide; 1HNMR (CDCl3): δ 7.93-7.80 (5H, m), 7.25-7.11 (4H, m), 7.09-7.01 (2H, m), 6.93-6.87 (2H, m), 6.56 (1H, s), 3.04 (3H, s), 2.45 (3H, s). MS (ESI): 467 (MH+). C. In a manner similar to that described for Example 20A, but replacing 4-methanesulfonyl-aniline with the appropriate amines in the last step, the following compounds were prepared:

Workup

  1. customthe following compound was prepared
  2. customthe following compounds were prepared

Sources & evidence

ORD record
ord-82ad1d6752c440d6ab70ed4124eb85cd
Source dataset
uspto-grants-2013_02
Patent number
US08367667B2

Reaction notes

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