Triethylamine → {4-[(3aR,6aR)-5-methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl]phenyl}(phenyl)methanone

HRID 12966

反応式

HRID 12966 の反応式
[CH3:1][N:2]1[CH2:9][C@@H:8]2[C@@H:4]([NH:5][CH2:6][CH2:7]2)[CH2:3]1.F[C:11]1[CH:24]=[CH:23][C:14]([C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:16])=[CH:13][CH:12]=1.C(N(CC)CC)C>C(#N)C.O>[CH3:1][N:2]1[CH2:9][C@@H:8]2[C@@H:4]([N:5]([C:20]3[CH:21]=[CH:22][C:17]([C:15]([C:14]4[CH:23]=[CH:24][CH:11]=[CH:12][CH:13]=4)=[O:16])=[CH:18][CH:19]=3)[CH2:6][CH2:7]2)[CH2:3]1

参加物

6

反応物 3

HCID 8471TriethylamineHCID 676634-FluorobenzophenoneHCID 44221716(3aR,6aR)-5-Methyloctahydropyrrolo[3,4-b]pyrrole

生成物 1

HCID 24743780{4-[(3aR,6aR)-5-methylhexahydropyrrolo[3,4-b]pyrrol-1(2H)-yl]phenyl}(phenyl)methanone

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

The product of Example 7B (35 mg, 0.28 mmole), 4-fluorobenzophenone (110 mg, 0.55 mmole) and triethylamine (200 μl, 1.43 mmole) were dissolved in 1 ml of acetonitrile and heated at 80° C. under N2 for 3 days. The mixture was cooled to room temperature, diluted with water and extracted with dichloromethane (5×). The combined organics were dried over sodium sulfate, filtered, concentrated under reduced pressure and purified by chromatography (eluting with a mixture of 5% methanol and 0.5% ammonium hydroxide in dichloromethane) to provide the title compound. 1H NMR (CDCl3) δ ppm 7.93 (d, J=8.82 Hz, 2H) 7.20-7.34 (m, 5H) 6.50 (d, J=9.16 Hz, 2H) 4.31-4.47 (m, 1H) 4.19 (s, 2H) 3.55-3.67 (m, 1H) 3.39-3.52 (m, 1H) 3.09-3.28 (m, 1H) 2.44-2.89 (m, 4H) 2.15-2.27 (m, 1H) 2.09 (s, 3H) 1.94-2.06 (m, 1H), MS (M+H)+=307.

後処理

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with dichloromethane (5×)
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. custompurified by chromatography (
  7. washeluting with a mixture of 5% methanol and 0.5% ammonium hydroxide in dichloromethane)

出典と根拠

ORDレコード
ord-3a3c6ff74c154728a22769369099a46b
出典データセット
uspto-grants-2010_06
特許番号
US07728031B2

関連ノート

読み込み中…