Triphenylphosphine → N-(1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethyl)-5-phenyloxazol-2-amine

HRID 1993608노트

반응식

HRID 1993608 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([F:29])[CH:20]=2)([N:16]=[C:17]=S)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:6][CH:7]=1.[N:30]([CH2:33][C:34]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:35])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([NH:16][C:17]2[O:35][C:34]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[CH:33][N:30]=2)([C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([F:29])[CH:20]=2)[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:6][CH:7]=1

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 109865532-Azido-1-phenylethanoneHCID 866129665-Chloro-2-(1-(3-fluoro-5-(trifluoromethyl)phenyl)-1-isothiocyanato-2-phenylethyl)pyridine

생성물 1

HCID 16743760N-(1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethyl)-5-phenyloxazol-2-amine수율 12%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
90 °C

실험 절차

5-chloro-2-(1-(3-fluoro-5-(trifluoromethyl)phenyl)-1-isothiocyanato-2-phenylethyl)pyridine (0.047 g, 0.108 mmol) in dioxane (3 mL) in a two drum vial was added 2-azido-1-phenylethanone (21 mg, 0.129 mmol) and solid bound triphenylphosphine (100 mg, 0.162 mmol). The reaction was heated at 90° C. for 1 hour. The reaction was concentrated and the crude mixture was purified by preparative HPLC (phenominex C18 column, 21×100 mm, 5μ) using MeOH/H2O (0.1% TFA) to give N-(1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethyl)-5-phenyloxazol-2-amine as a yellow solid (7 mg, 12% yield). LCMS: 4.1 min [M+1] 538.2 (4 min gradient, MeOH/H2O 0.1% TFA); 1H NMR (400 MHz, CDCl3) δ ppm 3.97-4.02 (m, 1H), 4.06-4.13 (m, 1H), 6.52 (d, J=7.58 Hz, 2H), 7.09 (t, J=7.46 Hz, 2H), 7.15 (s, 1H), 7.17 (dd, J=6.36, 1.71 Hz, 3H), 7.23 (d, J=8.56 Hz, 1H), 7.30-7.40 (m, 5H), 7.68-7.73 (m, 2H), 8.50 (d, J=2.20 Hz, 1H).

후처리

  1. concentrationThe reaction was concentrated
  2. customthe crude mixture was purified by preparative HPLC (phenominex C18 column, 21×100 mm, 5μ)

출처 및 근거

ORD 기록
ord-96536024a0bc4214ac5f169a2a08fea2
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652023B2

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