Methanesulfonyl chloride → 3-(1-Methylsulfonyl-trans-4-(2-pyridyl)-pyrrolidin-3-ylamino)-6-chloro-1-ethoxycarbonylmethylpyrazinone

HRID 398403ノート

反応式

HRID 398403 の反応式
C(OC([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C@H:10]([NH:19][C:20]2[C:21](=[O:33])[N:22]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:23]([Cl:26])=[CH:24][N:25]=2)[CH2:9]1)=O)(C)(C)C.CCN(C(C)C)C(C)C.[CH3:43][S:44](Cl)(=[O:46])=[O:45]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH3:43][S:44]([N:8]1[CH2:12][C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)[C@H:10]([NH:19][C:20]2[C:21](=[O:33])[N:22]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:23]([Cl:26])=[CH:24][N:25]=2)[CH2:9]1)(=[O:46])=[O:45]

参加物

6

反応物 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 700235713-(1-tert-Butyloxycarbonyl-trans-4-(2-pyridyl)-pyrrolidin-3-ylamino)-6-chloro-1-ethoxycarbonylmethylpyrazinone

生成物 1

HCID 120962303-(1-Methylsulfonyl-trans-4-(2-pyridyl)-pyrrolidin-3-ylamino)-6-chloro-1-ethoxycarbonylmethylpyrazinone

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 516892Sodium Bicarbonate溶媒

反応条件

温度
0 °C

実験手順

To a stirred solution of the hydrochloride salt of 3-(trans-4-(2-pyridyl)-pyrrolidin-3-ylamino)-6-chloro-1-ethoxycarbonylmethylpyrazinone from step 9 above (0.2 g, 0.48 mmol) in CH2Cl2 (20 mL) at 0° C. was added DIEA (0.30 mL, 1.7 mmol) and methanesulfonyl chloride (63 mg, 0.55 mmol). The resulting solution was stirred at 0° C. for 6 h and then at ambient temperature for 12 h. The mixture was diluted with CH2Cl2 and aqueous NaHCO3. The organic phase was separated, dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by column chromatography using a gradient elution of 2-4% MeOH:CH2Cl2 (0.20 g, TLC Rf=0.5, 95:5 CH2Cl2:MeOH; HPLC RT=5.47 min, method A).

後処理

  1. waitat ambient temperature for 12 h
  2. customThe organic phase was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography
  7. washa gradient elution of 2-4% MeOH

出典と根拠

ORDレコード
ord-156ef01714234d819d16f74ce98d78b7
出典データセット
uspto-grants-2003_08
特許番号
US06610692B1

反応ノート

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