Trifluoroacetic acid → 3-[4-(2,3-Difluoro-phenyl)-isoxazol-5-yl]-5-(4-morpholin-4-yl-cyclohex-1-enyl)-1H-pyrrolo[2,3-b]pyridine

HRID 269506ノート

反応式

HRID 269506 の反応式
[CH2:1]1[O:7][CH2:6][C@@H:4](O)[C@H:2]1O.I([O-])(=O)(=O)=O.[Na+].[F:14][C:15]1[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=1[C:22]1[CH:23]=[N:24][O:25][C:26]=1[C:27]1[C:35]2[C:30](=[N:31][CH:32]=[C:33]([C:36]3[CH2:41][CH2:40][CH:39]([NH2:42])[CH2:38][CH:37]=3)[CH:34]=2)[NH:29][CH:28]=1.C([BH3-])#N.[Na+].C(O)(C(F)(F)F)=O>O.CO>[F:14][C:15]1[C:20]([F:21])=[CH:19][CH:18]=[CH:17][C:16]=1[C:22]1[CH:23]=[N:24][O:25][C:26]=1[C:27]1[C:35]2[C:30](=[N:31][CH:32]=[C:33]([C:36]3[CH2:41][CH2:40][CH:39]([N:42]4[CH2:2][CH2:1][O:7][CH2:6][CH2:4]4)[CH2:38][CH:37]=3)[CH:34]=2)[NH:29][CH:28]=1

参加物

8

反応物 5

HCID 6422Trifluoroacetic acidHCID 6417731,4-AnhydroerythritolHCID 5003444Sodium cyanoborohydrideHCID 23667635Sodium periodateHCID 1354403634-{3-[4-(2,3-difluoro-phenyl)-isoxazol-5-yl]-1H-pyrrolo [2,3-b]pyridin-5-yl}-cyclohex-3-enylamine

生成物 1

HCID 1354579013-[4-(2,3-Difluoro-phenyl)-isoxazol-5-yl]-5-(4-morpholin-4-yl-cyclohex-1-enyl)-1H-pyrrolo[2,3-b]pyridine収率 36%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

A solution of 1,4-anhydroerythritol (208 mg, 2 mmol) in water was treated with sodium periodate (400 mg, 4 mmol)for 12 h, transferred to a solution of 4-{3-[4-(2,3-difluoro-phenyl)-isoxazol-5-yl]-1H-pyrrolo [2,3-b]pyridin-5-yl}-cyclohex-3-enylamine (50 mg, 0.12 mmol) in methanol (5 ml). The resulting solution was treated with sodium cyanoborohydride. After the reaction was completed, TFA was added, and the mixture was concentrated and purified by HPLC to give the morpholine product (20 mg) in 36% yield.

後処理

  1. concentrationthe mixture was concentrated
  2. custompurified by HPLC

出典と根拠

ORDレコード
ord-76c952c4dd2d4d5dbe21b65b0b9a4e06
出典データセット
uspto-grants-2008_11
特許番号
US07446199B2

反応ノート

読み込み中…