Sodium Bicarbonate → [(r)-3-(5,6-Difluoro-benzothiazol-2-ylamino)-pyrrolidin-1-yl]-(5-methyl-2-trifluoromethyl-phenyl)-methanone

HRID 598522

反応式

HRID 598522 の反応式
[F:1][C:2]1[C:3]([F:14])=[CH:4][C:5]2[S:9][C:8](S(C)=O)=[N:7][C:6]=2[CH:13]=1.[NH2:15][C@@H:16]1[CH2:20][CH2:19][N:18]([C:21]([C:23]2[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:24]=2[C:30]([F:33])([F:32])[F:31])=[O:22])[CH2:17]1.C([O-])(O)=O.[Na+]>CS(C)=O.O>[F:1][C:2]1[C:3]([F:14])=[CH:4][C:5]2[S:9][C:8]([NH:15][C@@H:16]3[CH2:20][CH2:19][N:18]([C:21]([C:23]4[CH:28]=[C:27]([CH3:29])[CH:26]=[CH:25][C:24]=4[C:30]([F:33])([F:31])[F:32])=[O:22])[CH2:17]3)=[N:7][C:6]=2[CH:13]=1

参加物

6

反応物 3

HCID 516892Sodium BicarbonateHCID 577489385,6-Difluoro-2-(methylsulfinyl)benzo[d]thiazoleHCID 57748952((R)-3-Amino-pyrrolidin-1-yl)-(5-methyl-2-trifluoromethyl-phenyl)-methanone2 回

生成物 1

HCID 42641617[(r)-3-(5,6-Difluoro-benzothiazol-2-ylamino)-pyrrolidin-1-yl]-(5-methyl-2-trifluoromethyl-phenyl)-methanone収率 47.6%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A mixture of 30 mg (0.129 mmol) rac-5,6-difluoro-2-methanesulfinyl-benzothiazole and 70.3 mg (0.258 mmol) ((R)-3-Amino-pyrrolidin-1-yl)-(5-methyl-2-trifluoromethyl-phenyl)-methanone (intermediate 13) in 540 μL dimethyl sulfoxide was heated in a 100° C. oil-bath for 4 h. The solution was cooled to room temperature, diluted with water and basified with a saturated NaHCO3 solution. The mixture was stirred for 1 h. The solid was filtered, washed with water and dissolved in dichloromethane. The solution was dried over Na2SO4, filtered and concentrated in vacuo. The crude compound was purified with flash column chromatography on silica eluting with a gradient formed from n-heptane and ethyl acetate to provide 27 mg (47.6%) of the title compound as a white solid. MS(m/e): 442.2 (M+H+).

後処理

  1. temperatureThe solution was cooled to room temperature
  2. filtrationThe solid was filtered
  3. washwashed with water
  4. dissolutiondissolved in dichloromethane
  5. dry with materialThe solution was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude compound was purified with flash column chromatography on silica eluting with a gradient
  9. customformed from n-heptane and ethyl acetate

出典と根拠

ORDレコード
ord-cfd520eb60e74003b6fef6c9257ca90f
出典データセット
uspto-grants-2011_03
特許番号
US07897627B2

関連ノート

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