Dimethylamine → (S)-5-chloro-6-(4-(3-(2-fluoro-4-(methylsulfonyl)phenylamino)-2-oxopyrrolidin-1-yl)piperidin-1-yl)-N,N-dimethylnicotinamide

HRID 408014ノート

反応式

HRID 408014 の反応式
[Cl:1][C:2]1[C:3]([N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[CH2:21][CH2:20][C@H:19]([NH:22][C:23]4[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][C:24]=4[F:33])[C:18]3=[O:34])[CH2:13][CH2:12]2)=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7](Cl)=[O:8].[CH3:35][NH:36][CH3:37]>CN(C=O)C.C(#N)C.C1COCC1.CCOC(C)=O>[Cl:1][C:2]1[C:3]([N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[CH2:21][CH2:20][C@H:19]([NH:22][C:23]4[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][C:24]=4[F:33])[C:18]3=[O:34])[CH2:13][CH2:12]2)=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([N:36]([CH3:37])[CH3:35])=[O:8]

参加物

5

反応物 2

HCID 674DimethylamineHCID 86688120(S)-5-chloro-6-(4-(3-(2-fluoro-4-(methylsulfonyl)phenylamino)-2-oxopyrrolidin-1-yl)piperidin-1-yl)nicotinoyl chloride

生成物 1

HCID 54670712(S)-5-chloro-6-(4-(3-(2-fluoro-4-(methylsulfonyl)phenylamino)-2-oxopyrrolidin-1-yl)piperidin-1-yl)-N,N-dimethylnicotinamide収率 39.3%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 86691292Dmf acn thf溶媒

実験手順

To a solution of (S)-5-chloro-6-(4-(3-(2-fluoro-4-(methylsulfonyl)phenylamino)-2-oxopyrrolidin-1-yl)piperidin-1-yl)nicotinoyl chloride (0.15 g, 0.28 mmol) in 5 mL of DMF/ACN/THF (1:1:1) was added dimethylamine (2 M solution in THF, 1.4 mL, 2.8 mmol) and the reaction was stirred at ambient temperature for 4 hours. The reaction was diluted with EtOAc (100 mL) and the organic layer was washed with water (20 mL) and brine (20 mL), and the organic layer was dried over MgSO4, and concentrated under vacuum. The material was triturated with isopropanol (about 6 mL) to give (S)-5-chloro-6-(4-(3-(2-fluoro-4-(methylsulfonyl)phenylamino)-2-oxopyrrolidin-1-yl)piperidin-1-yl)-N,N-dimethylnicotinamide (0.059 g, 0.11 mmol, 38% yield). Mass spectrum (apci) m/z=538.0 (M+H).

後処理

  1. washthe organic layer was washed with water (20 mL) and brine (20 mL)
  2. dry with materialthe organic layer was dried over MgSO4
  3. concentrationconcentrated under vacuum
  4. customThe material was triturated with isopropanol (about 6 mL)

出典と根拠

ORDレコード
ord-4f4b49fd18794cc582b2f033d713457f
出典データセット
uspto-grants-2014_06
特許番号
US08754226B2

反応ノート

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