Isopropylamine → Benzyl 3-(5-cyano-2-(isopropylamino)pyrimidin-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-ylcarbamate

HRID 40865ノート

反応式

HRID 40865 の反応式
[C:1]([C:3]1[C:4]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19]([NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:20]=3)[N:15]([S:33]([C:36]3[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=3)(=[O:35])=[O:34])[CH:14]=2)=[N:5][C:6](S(C)(=O)=O)=[N:7][CH:8]=1)#[N:2].[CH:43]([NH2:46])([CH3:45])[CH3:44].CCN(C(C)C)C(C)C>C1COCC1>[C:1]([C:3]1[C:4]([C:13]2[C:21]3[C:16](=[N:17][CH:18]=[C:19]([NH:22][C:23](=[O:32])[O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH:20]=3)[N:15]([S:33]([C:36]3[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=3)(=[O:35])=[O:34])[CH:14]=2)=[N:5][C:6]([NH:46][CH:43]([CH3:45])[CH3:44])=[N:7][CH:8]=1)#[N:2]

参加物

5

反応物 3

HCID 6363IsopropylamineHCID 81531DiisopropylethylamineHCID 68668408Benzyl 3-(5-cyano-2-(methylsulfonyl)pyrimidin-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-ylcarbamate

生成物 1

HCID 68668357Benzyl 3-(5-cyano-2-(isopropylamino)pyrimidin-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-ylcarbamate収率 82%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Benzyl 3-(5-cyano-2-(methylsulfonyl)pyrimidin-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-ylcarbamate (0.826 g, 1.372 mmol) in THF (30 mL) was treated with isopropylamine (0.234 mL, 2.744 mmol, 2.0 Eq) and DIPEA (0.478 mL, 2.744 mmol, 2.0 Eq) and allowed to heat at reflux for 1 hour. The mixture was concentrated in vacuo and purified by column chromatography (ISCO Companion™, 40 g column, 0-100% EtOAc/Petroleum ether) to give 0.651 g (82%) of the title compound.

後処理

  1. temperatureto heat
  2. temperatureat reflux for 1 hour
  3. concentrationThe mixture was concentrated in vacuo
  4. custompurified by column chromatography (ISCO Companion™, 40 g column, 0-100% EtOAc/Petroleum ether)

出典と根拠

ORDレコード
ord-8f4f1c8229fe4d978dccad9f31d02a0e
出典データセット
uspto-grants-2013_09
特許番号
US08530489B2

反応ノート

読み込み中…