Diisopropylethylamine → N-(1-(5-Chloro-2-(pyridin-2-yl)quinolin-3-yl)ethyl)-9H-purin-6-amine

HRID 1397715

반응식

HRID 1397715 반응식
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH:18]([NH2:20])[CH3:19])[C:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)=[N:7]2.Br[C:22]1[N:30]=[CH:29][N:28]=[C:27]2[C:23]=1[NH:24][CH:25]=[N:26]2.CCN(C(C)C)C(C)C>C(O)CCC>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH:18]([NH:20][C:22]1[N:30]=[CH:29][N:28]=[C:27]3[C:23]=1[N:24]=[CH:25][NH:26]3)[CH3:19])[C:6]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)=[N:7]2

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 5287830Purine, 6-bromo-HCID 577079431-(5-Chloro-2-(pyridin-2-yl)quinolin-3-yl)ethanamine

생성물 1

HCID 178463528N-(1-(5-Chloro-2-(pyridin-2-yl)quinolin-3-yl)ethyl)-9H-purin-6-amine수율 69%

시약·촉매·용매 1

HCID 2631-Butanol용매

반응 조건

온도
110 °C

실험 절차

Added 1-(5-chloro-2-(pyridin-2-yl)quinolin-3-yl)ethanamine (103 mg, 363 μmol), 6-bromopurine (72 mg, 363 μmol), n-butanol (2 mL) and DIPEA (190 μl, 1089 μmol) to a 10 mL flask. Submerged in an oil bath and heated at 110° C. for 40 h. The reaction mixture was concentrated on the rotavap to ˜0.5 mL of solvent, diluted with DCM, and chromatographed with 0-15% MeOH:DCM on 12 g silica gel column. The desired fractions were combined and concentrated to an oil which was dissolved in ACN:H2O and lyophilized to obtained 100 mg (69%) of a light tan solid. LC-MS (+esi, M+H4=402.1).

후처리

  1. customSubmerged in an oil bath
  2. concentrationThe reaction mixture was concentrated on the rotavap to ˜0.5 mL of solvent
  3. additiondiluted with DCM
  4. customchromatographed with 0-15% MeOH
  5. concentrationconcentrated to an oil which
  6. dissolutionwas dissolved in ACN

출처 및 근거

ORD 기록
ord-ea4503ed1e234dd5ad346c94085d3b16
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901135B2

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