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 269506노트

반응식

HRID 269506 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

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.

후처리

  1. concentrationthe mixture was concentrated
  2. custompurified by HPLC

출처 및 근거

ORD 기록
ord-76c952c4dd2d4d5dbe21b65b0b9a4e06
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07446199B2

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