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Potassium Carbonate → (R)-2-[2,4-dioxo-1-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-1,4-dihydro-2H-quinazolin-3-yl]-pentanoic acid methyl ester

HRID 388473
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HRID 388473 반응식
[CH3:1][O:2][C:3](=[O:20])[C@H:4]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]1=[O:19])[CH2:5][CH2:6][CH3:7].C[C:22]1[C:23]([CH3:38])=[C:24](C)[C:25]([CH3:36])=[C:26]2[C:30]=1[N:29]([CH3:31])[C:28](C)=[C:27]2[CH2:33]NI.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:20])[C@H:4]([N:8]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH2:33][C:27]2[C:26]3[C:30](=[CH:22][C:23]([CH3:38])=[CH:24][C:25]=3[CH3:36])[N:29]([CH3:31])[CH:28]=2)[C:9]1=[O:19])[CH2:5][CH2:6][CH3:7]
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 68726798(R)-2-(2,4-Dioxo-1,4-dihydro-2H-quinazolin-3-yl)-pentanoic acid methyl esterHCID 131730211trimethyl-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-amino iodide

생성물 1

HCID 68745323(R)-2-[2,4-dioxo-1-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-1,4-dihydro-2H-quinazolin-3-yl]-pentanoic acid methyl ester수율 80.7%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

반응 조건

온도
100 °C

실험 절차

To a solution of (R)-2-(2,4-Dioxo-1,4-dihydro-2H-quinazolin-3-yl)-pentanoic acid methyl ester (50 mg, 0.18 mmol) (prepared according to example 1, steps 1-3) in DMF (10 mL) are added trimethyl-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-amino iodide (97 mg, 0.27 mmol) and K2CO3 (50 mg, 0.36 mmol) at room temperature. The solution is heated to 100° C. for 4 hours. The solution is cooled and is extracted with water and EtOAc. The combined organic layer is dried with MgSO4 and is filtered. The filtrate is concentrated and the residue is purified by flash chromatography with 20% EtOAc in Hexane as the eluent to afford (R)-2-[2,4-dioxo-1-(1,4,6-trimethyl-1H-indol-3-ylmethyl)-1,4-dihydro-2H-quinazolin-3-yl]-pentanoic acid methyl ester (65 mg, 80%) as a white foam.

후처리

  1. temperatureThe solution is cooled
  2. extractionis extracted with water and EtOAc
  3. dry with materialThe combined organic layer is dried with MgSO4
  4. filtrationis filtered
  5. concentrationThe filtrate is concentrated
  6. customthe residue is purified by flash chromatography with 20% EtOAc in Hexane as the eluent

출처 및 근거

ORD 기록
ord-8e2484668a184771af1b0793a73d1ee9
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08377949B2

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