Triethylamine → (R)-4-[2-(6-Cyano-3,3-dimethyl-2,3-dihydro-indol-1-yl)-2-oxo-ethyl]-2-methyl-piperazine-1-carboxylic acid tert-butyl ester

HRID 1475410노트

반응식

HRID 1475410 반응식
Cl[CH2:2][C:3]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]#[N:15])[CH:12]=2)[C:7]([CH3:17])([CH3:16])[CH2:6]1)=[O:4].[CH3:18][C@@H:19]1[CH2:24][NH:23][CH2:22][CH2:21][N:20]1[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26].C(N(CC)CC)C>C(#N)C>[C:28]([O:27][C:25]([N:20]1[CH2:21][CH2:22][N:23]([CH2:2][C:3]([N:5]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([C:14]#[N:15])[CH:12]=3)[C:7]([CH3:17])([CH3:16])[CH2:6]2)=[O:4])[CH2:24][C@H:19]1[CH3:18])=[O:26])([CH3:31])([CH3:29])[CH3:30]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 10262201tert-Butyl (2R)-2-methylpiperazine-1-carboxylateHCID 867240061-(2-Chloroacetyl)-3,3-dimethylindoline-6-carbonitrile

생성물 1

HCID 70981803(R)-4-[2-(6-Cyano-3,3-dimethyl-2,3-dihydro-indol-1-yl)-2-oxo-ethyl]-2-methyl-piperazine-1-carboxylic acid tert-butyl ester수율 175.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
50 °C

실험 절차

To a solution of 1-(2-chloroacetyl)-3,3-dimethylindoline-6-carbonitrile (0.10 g, 0.40 mmol) and (R)-tert-butyl 2-methylpiperazine-1-carboxylate (0.088 g, 0.41 mmol) in acetonitrile (1.5 mL) was added triethylamine (0.083 mL, 0.6 mmol). The reaction mixture was heated at 50° C. for 3 h. The reaction mixture was then cooled and concentrated. The reaction was repeated on a 0.6 mmol scale and the combined crude material was purified by flash column chromatography, eluting with 20% EtOAc in heptane, to give the title compound (0.29 g) [M+H]+=413.

후처리

  1. temperatureThe reaction mixture was then cooled
  2. concentrationconcentrated
  3. customwas purified by flash column chromatography
  4. washeluting with 20% EtOAc in heptane

출처 및 근거

ORD 기록
ord-ee3429768187433e975037b806b934f3
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018214B2

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