Triethylamine → 3-(2,5-Dimethyl-benzenesulfonyl)-8-(4-phenyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane

HRID 1193137노트

반응식

HRID 1193137 반응식
[C:1]1([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([N:13]3[CH:20]4[CH:15]([CH2:16][CH2:17][NH:18][CH2:19]4)[CH2:14]3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=1[S:29](Cl)(=[O:31])=[O:30].CCN(CC)CC>C(Cl)Cl>[CH3:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=1[S:29]([N:18]1[CH2:17][CH2:16][CH:15]2[CH:20]([N:13]([C:9]3[N:8]=[C:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[CH:12]=[CH:11][N:10]=3)[CH2:14]2)[CH2:19]1)(=[O:30])=[O:31]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 87910Benzenesulfonyl chloride, 2,5-dimethyl-HCID 671167498-(4-Phenyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane2회

생성물 1

HCID 529204073-(2,5-Dimethyl-benzenesulfonyl)-8-(4-phenyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane수율 35%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

A mixture of 8-(4-phenyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane (Intermediate 6, 110 mg, 0.29 mmol), 2,5-dimethyl-benzenesulfonyl chloride (83 mg, 0.41 mmol) and Et3N (91 mg, 0.9 mmol) was stirred in DCM (5.0 mL) at RT for 18 h. The reaction mixture was diluted with more DCM (15 mL) and washed with water. The organic layers were combined, dried, filtered and concentrated under reduced pressure to yield crude product. The crude product was purified on HPLC (basic system) to yield the title compound (40 mg, 35%). MS (ESI) mass calcd. for C24H26N4O2S, 434.55; m/z found 435.3 [M+H]+. 1H NMR (400 MHz, CDCl3): 8.26 (s br, 1H), 7.87 (s br, 2H), 7.70 (s, 1H), 7.51-7.34 (m, 3H), 6.94 (d, J=5.3, 1H), 6.91-6.73 (m, 2H), 4.62-4.52 (m, 1H), 4.16 (t, J=8.3, 1H), 4.04 (dd, J=13.5, 2.9, 1H), 3.93 (dd, J=8.6, 3.9, 1H), 3.85-3.73 (m, 1H), 3.74-3.59 (m, 1H), 3.40 (dd, J=13.5, 2.8, 1H), 2.95-2.89 (m, 1H), 2.45 (s, 3H), 2.28-2.12 (m, 1H), 2.21-1.85 (m, 4H).

후처리

  1. washwashed with water
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto yield crude product
  6. customThe crude product was purified on HPLC (basic system)

출처 및 근거

ORD 기록
ord-251f58e65e9945dfa7d815ffb8fcf897
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680275B2

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