5-(Trifluoromethyl)dibenzothiophen-5-ium-3-sulfonate → 2-[(S)-1-Phenylethylamino]-4-[4-trifluoromethyl-5-aminobenzimidazol-1-yl]pyrimidine

HRID 2300797노트

반응식

HRID 2300797 반응식
[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([NH2:25])=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:26][C:27]([F:46])([F:45])[S+]1C2C=CC=CC=2C2C=CC(S([O-])(=O)=O)=CC1=2>CN(C=O)C>[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[CH:22][C:23]([NH2:25])=[C:24]([C:27]([F:46])([F:45])[F:26])[C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

4

반응물 2

HCID 27774995-(Trifluoromethyl)dibenzothiophen-5-ium-3-sulfonateHCID 98839772-[(S)-1-phenylethylamino]-4-[5-aminobenzimidazol-1-yl]pyrimidine

생성물 1

HCID 599249592-[(S)-1-Phenylethylamino]-4-[4-trifluoromethyl-5-aminobenzimidazol-1-yl]pyrimidine수율 23.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

To a stirred solution of 2-[(S)-1-phenylethylamino]-4-[5-amino-benzimidazol-1-yl]pyrimidine (330 mg, 1 mmol, 1 eq) in DMF (2 mL) was added S-(trifluoromethyl)-dibenzothiophenium-3-sulfonate (166 mg, 0.5 mmol, 0.5 eq) and the mixture was heated to 80° C. for 7 hours. The reaction was cooled and the DMF was removed under reduced pressure. The residue was diluted with water and extracted wth CH2Cl2. The organic extracts were combined, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The product was purified by column chromatography (eluted with 3.5% MeOH/CH2Cl2) followed by preparative thin layer chromatography (eluted 2× with 3.5% MeOH/CH2Cl2) to give 46 mg of the title compound. 1H NMR (500 MHz, CDCl3): δ 1.63 (3H, d, J=7 Hz), 4.32 (3H, s), 5.13 (1H, br s), 5.80 (1H, br s), 6.62 (1H, br), 6.70 (1H, d, J=5.5 Hz), 7.29 (1H, m), 7.39 (2H, t, J=7.5 Hz), 7.43 (2H, d, J=7 Hz), 7.62 (1H, br), 8.38 (1H, d, J=5.5 Hz), 8.40 (1H, br). Mass spectrum (ESI) 398.14 (M+1).

후처리

  1. temperatureThe reaction was cooled
  2. customthe DMF was removed under reduced pressure
  3. additionThe residue was diluted with water
  4. extractionextracted wth CH2Cl2
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe product was purified by column chromatography (eluted with 3.5% MeOH/CH2Cl2)
  9. washfollowed by preparative thin layer chromatography (eluted 2× with 3.5% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-ced5a082381d4a2abb92cf2ff2df1a61
출처 데이터셋
uspto-grants-2002_12
특허 번호
US06498165B1

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