Ethyl diazoacetate → Ethyl N-{1-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]piperidin-4-yl}-N-[(2E)-3-(2,5-difluorophenyl)prop-2-en-1-yl]glycinate

HRID 1644380노트

반응식

HRID 1644380 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1/[CH:9]=[CH:10]/[CH2:11][NH:12][CH:13]1[CH2:18][CH2:17][N:16]([CH2:19][CH2:20][N:21]2[C:26]3[CH:27]=[C:28]([C:31]#[N:32])[CH:29]=[CH:30][C:25]=3[O:24][CH2:23][C:22]2=[O:33])[CH2:15][CH2:14]1.[N+](=[CH:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])=[N-]>ClCCl.C([O-])(=O)C.[Rh+2].C([O-])(=O)C>[C:31]([C:28]1[CH:29]=[CH:30][C:25]2[O:24][CH2:23][C:22](=[O:33])[N:21]([CH2:20][CH2:19][N:16]3[CH2:17][CH2:18][CH:13]([N:12]([CH2:11]/[CH:10]=[CH:9]/[C:3]4[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=4[F:1])[CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:14][CH2:15]3)[C:26]=2[CH:27]=1)#[N:32]

참가 물질

5

반응물 2

HCID 12192Ethyl diazoacetateHCID 119832164-[2-(4-{[(2E)-3-(2,5-difluorophenyl)prop-2-en-1-yl]amino}piperidin-1-yl)ethyl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrile

생성물 1

HCID 15982020Ethyl N-{1-[2-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)ethyl]piperidin-4-yl}-N-[(2E)-3-(2,5-difluorophenyl)prop-2-en-1-yl]glycinate수율 5%

시약·촉매·용매 2

HCID 21674Acetic acid, rhodium(2+) salt촉매HCID 6344Dichloromethane용매

실험 절차

To a mixture of 4-[2-(4-{[(2E)-3-(2,5-difluorophenyl)prop-2-en-1-yl]amino}piperidin-1-yl)ethyl]-3-oxo-3,4-dihydro-2H-1,4-benzoxazine-6-carbonitrile (Example 37) (120 mg, 0.265 mmol) and ethyl diazoacetate (0.09 mL) in dichloromethane (5 ml) was added rhodium(II) acetate (4 mg, 0.009 mmol) at room temperature. After 72 hrs, the product was concentrated and purified by preparative TLC to give 6.7 mg of product (5%).

후처리

  1. concentrationthe product was concentrated
  2. custompurified by preparative TLC

출처 및 근거

ORD 기록
ord-0d8963adb00145d888df0113455127f1
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124602B2

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