Methanol → Ethyl 4-(1-(2-(4-(trifluoromethyl)phenyl)pyrimidin-5-ylamino)butyl)benzoate

HRID 2173816노트

반응식

HRID 2173816 반응식
CO.[C:3]([C:8]1[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=1)(=O)[CH2:4][CH2:5][CH3:6].[F:19][C:20]([F:35])([F:34])[C:21]1[CH:26]=[CH:25][C:24]([C:27]2[N:32]=[CH:31][C:30]([NH2:33])=[CH:29][N:28]=2)=[CH:23][CH:22]=1.[B][B][B][B][B][B][B][B][B][B]>Cl>[F:35][C:20]([F:19])([F:34])[C:21]1[CH:22]=[CH:23][C:24]([C:27]2[N:28]=[CH:29][C:30]([NH:33][CH:3]([C:8]3[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=3)[CH2:4][CH2:5][CH3:6])=[CH:31][N:32]=2)=[CH:25][CH:26]=1

참가 물질

6

반응물 4

HCID 887MethanolHCID 431422772-(4-(Trifluoromethyl)phenyl)pyrimidin-5-amineHCID 67980577Ethyl 4-butyrylbenzoateHCID 178419135HCID 178419135, 화합물

생성물 1

HCID 67981358Ethyl 4-(1-(2-(4-(trifluoromethyl)phenyl)pyrimidin-5-ylamino)butyl)benzoate수율 24%

시약·촉매·용매 1

HCID 313Hydrochloric Acid용매

실험 절차

Methanol (0.70 mL) was added to a flask containing ethyl 4-butyrylbenzoate (82.8 mg, 0.376 mmol), 2-(4-(trifluoromethyl)phenyl)pyrimidin-5-amine (90.0 mg, 0.376 mmol) and decaborane (46.0 mg, 0.376 mmol) at room temperature under nitrogen. The resulting solution was stirred at room temperature overnight. The mixture was diluted with 1N HCl and extracted with ethyl acetate twice. The combined organic layers were dried over sodium sulfate, filtered and concentrated. Purification by column chromatography (0-35% ethyl acetate in heptane) gave ethyl 4-(1-(2-(4-(trifluoromethyl)phenyl)pyrimidin-5-ylamino)butyl)benzoate (40.0 mg, 24%). 1H NMR (400 MHz, CDCl3, δ): 8.32 (d, J=8.19 Hz, 2H), 8.07 (s, 2H), 7.98-8.04 (m, 2H), 7.63 (d, J=8.19 Hz, 2H), 7.36-7.41 (m, 2H), 4.38-4.43 (m, 2H), 4.35 (q, J=7.02 Hz, 2H), 1.75-1.91 (m, 2H), 1.36 (t, J=7.02 Hz, 3H), 1.20-1.52 (m, 2H), 0.94 (t, J=7.32 Hz, 2H). MS (M+1): 444.3.

후처리

  1. extractionextracted with ethyl acetate twice
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by column chromatography (0-35% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-15cfa183555b45518174946394c1b8a7
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056834B2

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