Acetic Acid → 5-chloro-thiophene-2-carboxylic acid {(1S,4R)-4-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-2-pyrrolidin-1-yl-cyclopentyl}-amide

HRID 2244690ノート

反応式

HRID 2244690 の反応式
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[O:14])[CH:5]=[CH:4][C:3]=1[NH:15][C:16]([C@@H:18]1[CH2:22][C@H:21]([NH:23][C:24]([C:26]2[S:27][C:28]([Cl:31])=[CH:29][CH:30]=2)=[O:25])[C:20](=O)[CH2:19]1)=[O:17].[NH:33]1[CH2:37][CH2:36][CH2:35][CH2:34]1.C(O)(=O)C.[BH3-]C#N.[Na+]>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]2=[O:14])[CH:5]=[CH:4][C:3]=1[NH:15][C:16]([C@@H:18]1[CH2:22][C@H:21]([NH:23][C:24]([C:26]2[S:27][C:28]([Cl:31])=[CH:29][CH:30]=2)=[O:25])[CH:20]([N:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)[CH2:19]1)=[O:17]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 31268PyrrolidineHCID 5003444Sodium cyanoborohydrideHCID 588264485-chloro-thiophene-2-carboxylic acid {(1S,4R)-4-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-2-oxo-cyclopentyl}-amide

生成物 1

HCID 588264295-chloro-thiophene-2-carboxylic acid {(1S,4R)-4-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-2-pyrrolidin-1-yl-cyclopentyl}-amide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of 5-chloro-thiophene-2-carboxylic acid {(1S,4R)-4-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-2-oxo-cyclopentyl}-amide (75 mg) in THF (3 ml) were added pyrrolidine (0.03 ml) and acetic acid (0.02 ml). After stirring for 1 hr at r.t., NaBH3CN (11 mg) was added and stirring of the yellow reaction mixture was continued over night, then concentrated. The crude product was purified by column chromatography (silica gel; gradient: CH2Cl2→CH2Cl2MeOH 85:15) to give 5-chloro-thiophene-2-carboxylic acid {(1S,4R)-4-[2-fluoro-4-(2-oxo-2H-pyridin-1-yl)-phenylcarbamoyl]-2-pyrrolidin-1-yl-cyclopentyl}-amide (40 mg) as crystalline solid. MS 529.3 ([M+H]+).

後処理

  1. stirringstirring of the yellow reaction mixture
  2. waitwas continued over night
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography (silica gel; gradient: CH2Cl2→CH2Cl2MeOH 85:15)

出典と根拠

ORDレコード
ord-d1fd826db8b14aaba690de29a1a7ead5
出典データセット
uspto-grants-2010_03
特許番号
US07678917B2

反応ノート

読み込み中…