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Diisopropylethylamine → (R)-(1-(6-chloropyridin-3-yl)ethylamino)-4-(1-tosyl-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrile

HRID 1853460
ノート
印刷プレビュー

反応式

HRID 1853460 の反応式
C(N(C(C)C)CC)(C)C.CS([C:14]1[N:19]=[C:18]([C:20]2[C:28]3[C:23](=[N:24][CH:25]=[C:26]([C:29]([F:32])([F:31])[F:30])[CH:27]=3)[N:22]([S:33]([C:36]3[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=3)(=[O:35])=[O:34])[CH:21]=2)[C:17]([C:43]#[N:44])=[CH:16][N:15]=1)(=O)=O.[Cl:45][C:46]1[N:51]=[CH:50][C:49]([CH:52]([NH2:54])[CH3:53])=[CH:48][CH:47]=1>O1CCCC1>[Cl:45][C:46]1[N:51]=[CH:50][C:49]([C@H:52]([NH:54][C:14]2[N:19]=[C:18]([C:20]3[C:28]4[C:23](=[N:24][CH:25]=[C:26]([C:29]([F:30])([F:32])[F:31])[CH:27]=4)[N:22]([S:33]([C:36]4[CH:37]=[CH:38][C:39]([CH3:40])=[CH:41][CH:42]=4)(=[O:35])=[O:34])[CH:21]=3)[C:17]([C:43]#[N:44])=[CH:16][N:15]=2)[CH3:53])=[CH:48][CH:47]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 81531DiisopropylethylamineHCID 157456051-(6-Chloropyridin-3-yl)ethan-1-amineHCID 594143252-Methylsulfonyl-4-[1-(p-tolylsulfonyl)-5-(trifluoromethyl)-pyrrolo[5,4-b]pyridin-3-yl]pyrimidine-5-carbonitrile

生成物 1

HCID 86643592(R)-(1-(6-chloropyridin-3-yl)ethylamino)-4-(1-tosyl-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrile収率 58%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
110 °C

実験手順

Diisopropylethylamine (730 μl, 4.2 mmol) was added to a mixture of 2-(methylsulfonyl)-4-(1-tosyl-5-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)pyrimidine-5-carbonitrile (330 mg, 2.1 mmol) and 1-(6-chloropyridin-3-yl)ethanamine (described in the literature: EP 375907 (B1)) (500 mg, 1 mmol) in tetrahydrofuran (3 mL). The reaction mixture was heated under microwave irradiation at 110° C. for 15 minutes. The reaction mixture was partitioned between EtOAc and water. The organic phase was dried over magnesium sulphate, filtered and evaporated to dryness. The residue was purified on silica gel by flash column chromatography to afford the title compound as a wax (345 mg, 58% yield).

後処理

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe residue was purified on silica gel by flash column chromatography

出典と根拠

ORDレコード
ord-152f341ba3f846bba9265a833cb993e4
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08962642B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート