홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

Ammonium formate → tert-butyl (2R)-2-({[5-methyl-4-(2-{[(3-methyl-1H-indol-5-yl)methyl]amino}-2-oxoethyl)-3-oxo-3,4-dihydro-2-pyrazinyl]amino}methyl)-1-pyrrolidinecarboxylate

HRID 567825
노트
인쇄 미리보기

반응식

HRID 567825 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][NH:14][C:15]1[C:16](=[O:26])[N:17]([CH2:22][C:23](O)=[O:24])[C:18]([CH3:21])=[CH:19][N:20]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:27][C:28]1[C:36]2[C:31](=[CH:32][CH:33]=[C:34]([CH2:37][NH2:38])[CH:35]=2)[NH:30][CH:29]=1.C([O-])=O.[NH4+]>[Pd].ClCCl>[CH3:21][C:18]1[N:17]([CH2:22][C:23]([NH:38][CH2:37][C:34]2[CH:35]=[C:36]3[C:31](=[CH:32][CH:33]=2)[NH:30][CH:29]=[C:28]3[CH3:27])=[O:24])[C:16](=[O:26])[C:15]([NH:14][CH2:13][C@H:9]2[CH2:10][CH2:11][CH2:12][N:8]2[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[N:20][CH:19]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 2723923Ammonium formateHCID 18470813(3-methyl-1H-indol-5-yl)methanamineHCID 599006292-[3-({[(2R)-1-(tert-butoxycarbonyl)pyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]acetic acid

생성물 1

HCID 59900555tert-butyl (2R)-2-({[5-methyl-4-(2-{[(3-methyl-1H-indol-5-yl)methyl]amino}-2-oxoethyl)-3-oxo-3,4-dihydro-2-pyrazinyl]amino}methyl)-1-pyrrolidinecarboxylate수율 44%

시약·촉매·용매 2

HCID 23938Palladium촉매2회
HCID 6344Dichloromethane용매

실험 절차

The title compound was prepared by a similar method to preparation 45 from 2-[3-({[(2R)-1-(tert-butoxycarbonyl)pyrrolidinyl]methyl}amino)-6-methyl-2-oxo-1(2H)-pyrazinyl]acetic acid [see preparation 54] and (3-methyl-1H-indol-5-yl)methylamine (72 mg, 0.45 mmol) [see preparation 36]. The crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol (100:0) changing to (95:5) in 1% increments 1H-NMR indicated starting chloro compound material. A mixture of this product with 10% palladium on charcoal (39.6 mg) and ammonium formate (439.5 mg,6.98 mmol) in dichloromethane (50 ml), was then stirred at room temperature overnight. Additional, 10% Palladium on charcoal (49 mg) was added and the mixture was heated under reflux for 48 hrs, after which time the catalyst was filtered off and the solvent evaporated under reduced pressure. The residue was partitioned between ethyl acetate (100 ml) and water (100 ml). The organic layer was separated and dried over MgSO4 and the solvent evaporated under reduced pressure to afford the title compound as a off-white solid, (44%).

후처리

  1. customThe crude product was purified by column chromatography on silica gel using an elution gradient of dichloromethane:methanol (100:0)
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 48 hrs
  4. filtrationafter which time the catalyst was filtered off
  5. customthe solvent evaporated under reduced pressure
  6. customThe residue was partitioned between ethyl acetate (100 ml) and water (100 ml)
  7. customThe organic layer was separated
  8. dry with materialdried over MgSO4
  9. customthe solvent evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-891a47a3bac841aaaf8d8ead4354b925
출처 데이터셋
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06180627B2

반응 노트

불러오는 중…

이 페이지에서참가 물질실험 절차후처리출처 및 근거반응 노트