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

HRID 1193137ノート

反応式

HRID 1193137 の反応式
[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]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 87910Benzenesulfonyl chloride, 2,5-dimethyl-HCID 671167498-(4-Phenyl-pyrimidin-2-yl)-3,8-diaza-bicyclo[4.2.0]octane2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-251f58e65e9945dfa7d815ffb8fcf897
出典データセット
uspto-grants-2014_03
特許番号
US08680275B2

反応ノート

読み込み中…