Dimethyl Sulfide → 3-(3,5-Difluorophenyl)-2-[2'-(3-methoxypropyl)-3-methylbiphenyl-4-yl]propan-1-amine

HRID 2194926노트

반응식

HRID 2194926 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH2:25][CH2:26][CH2:27][O:28][CH3:29])=[CH:15][C:14]=2[CH3:30])[C:11]#[N:12])[CH:5]=[C:6]([F:8])[CH:7]=1.CSC>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[CH2:25][CH2:26][CH2:27][O:28][CH3:29])=[CH:15][C:14]=2[CH3:30])[CH2:11][NH2:12])[CH:5]=[C:6]([F:8])[CH:7]=1

참가 물질

4

반응물 2

HCID 1068Dimethyl SulfideHCID 674487153-(3,5-Difluorophenyl)-2-[2'-(3-methoxypropyl)-3-methylbiphenyl-4-yl]propanenitrile

생성물 1

HCID 584884533-(3,5-Difluorophenyl)-2-[2'-(3-methoxypropyl)-3-methylbiphenyl-4-yl]propan-1-amine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 3-(3,5-difluorophenyl)-2-[2′-(3-methoxypropyl)-3-methylbiphenyl-4-yl]propanenitrile from step 3 (1 eq.) in THF (0.1M) was added borane-dimethyl sulfide complex (5 eq.). The mixture was refluxed for 5 h without a condensor to release the dimethylsulfide. The final concentration was 0.2M. The mixture was cooled to room temperature, quenched slowly with HCl (1N). The pH was set to 10 using NaOH (1N) and finally the mixture was extracted with CH2Cl2. The organic extract was dried over Na2SO4 filtered and concentrated. Purification by column chromatography on silica gel eluting with CH2Cl2/MeOH(NH3; 2M) 5% afforded the desired compound as a colorless oil. 1H NMR (500 MHz, CD3OD): δ 7.42 (d, 1H), 7.30-7.26 (m, 2H), 7.23-7.20 (m, 2H), 7.12 (d, 1H), 7.04 (s, 1H), 6.76-6.72 (m, 1H), 6.66-6.63 (m, 2H), 3.53-3.50 (m, 1H), 3.25-3.20 (m, 7H), 3.15 (dd, 1H), 2.88 (dd, 1H), 2.65 (d, 1H), 2.64 (d, 1H), 2.12 (s, 3H), 1.70-1.65 (m, 2H).

후처리

  1. temperatureThe mixture was refluxed for 5 h without a condensor
  2. customquenched slowly with HCl (1N)
  3. extractionfinally the mixture was extracted with CH2Cl2
  4. extractionThe organic extract
  5. dry with materialwas dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by column chromatography on silica gel eluting with CH2Cl2/MeOH(NH3; 2M) 5%

출처 및 근거

ORD 기록
ord-7d9f6ef02cba4365adfc558700baadf1
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08334308B2

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