Triethylamine → N-[3,5-bis(trifluoromethyl)phenyl]-4-(2-{[(2,3,5,6-tetrafluoropyridin-4-yl)amino]methyl}phenyl)piperazine-1-carboxamide

HRID 907570Notes

Reaction equation

HRID 907570 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([N:16]2[CH2:21][CH2:20][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH2:28][NH2:29])[CH2:18][CH2:17]2)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(N(CC)CC)C.[F:39][C:40]1[N:45]=[C:44]([F:46])[C:43]([F:47])=[C:42](F)[C:41]=1[F:49]>C(#N)C.CO>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([NH:13][C:14]([N:16]2[CH2:17][CH2:18][N:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH2:28][NH:29][C:42]3[C:41]([F:49])=[C:40]([F:39])[N:45]=[C:44]([F:46])[C:43]=3[F:47])[CH2:20][CH2:21]2)=[O:15])[CH:4]=[C:3]([C:2]([F:1])([F:30])[F:31])[CH:8]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 69690PentafluoropyridineHCID 590139384-(2-Aminomethyl-phenyl)piperazine-1-carboxylic acid (3,5-bis-trifluoromethyl-phenyl)amide

Product 1

HCID 59013863N-[3,5-bis(trifluoromethyl)phenyl]-4-(2-{[(2,3,5,6-tetrafluoropyridin-4-yl)amino]methyl}phenyl)piperazine-1-carboxamideYield 67.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

4-(2-Aminomethyl-phenyl)piperazine-1-carboxylic acid (3,5-bis-trifluoromethyl-phenyl)amide (50 mg, 0.11 mmol) was dissolved in 500 mL of acetonitrile. Then, triethylamine (20 L, 0.14 mmol) was added, followed by pentafluoropyridine (16 μL, 0.15 mmol). The reaction was stirred at room temperature overnight. The reaction mixture was diluted to 2 mL in volume with methanol and the mixture was purified by reverse phase HPLC to give 44 mg of the product as a white solid. 1H NMR (CDCl3) δ 7.87 (s, 2H), 7.51 (s, 1H), 7.29-7.36 (m, 2H), 7.16-7.21 (m, 2H), 6.78 (s, 1H), 5.90 (br s, 1H), 4.79 (d, 2H), 3.71 (m, 4H), 3.02 (t, 4H) ppm.

Workup

  1. customthe mixture was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-7a87b9aceb014e53a6f72d42be8d4c72
Source dataset
uspto-grants-2011_09
Patent number
US08013156B2

Reaction notes

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