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

HRID 907570
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HRID 907570 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 887
Methanol
용매
HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  1. customthe mixture was purified by reverse phase HPLC

출처 및 근거

ORD 기록
ord-7a87b9aceb014e53a6f72d42be8d4c72
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08013156B2

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