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Diisopropylethylamine → 4-(Benzyloxy)-1-(9-methyl-2-(2-(pyrrolidin-1-yl)ethyl)-2,3,4,9,-tetrahydro-1h-pyrido[3,4-b]indol-7-yl)pyridine-2(1h)-one

HRID 1020679
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HRID 1020679 반응식
Cl.Cl[CH2:3][CH2:4][N:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1.[CH2:10]([O:17][C:18]1[CH:23]=[CH:22][N:21]([C:24]2[CH:32]=[C:31]3[C:27]([C:28]4[CH2:37][CH2:36][NH:35][CH2:34][C:29]=4[N:30]3[CH3:33])=[CH:26][CH:25]=2)[C:20](=[O:38])[CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(C(C)C)CC)(C)C>CCO>[CH2:10]([O:17][C:18]1[CH:23]=[CH:22][N:21]([C:24]2[CH:32]=[C:31]3[C:27]([C:28]4[CH2:37][CH2:36][N:35]([CH2:3][CH2:4][N:5]5[CH2:9][CH2:8][CH2:7][CH2:6]5)[CH2:34][C:29]=4[N:30]3[CH3:33])=[CH:26][CH:25]=2)[C:20](=[O:38])[CH:19]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1
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5

반응물 3

HCID 81531DiisopropylethylamineHCID 816681-(2-Chloroethyl)pyrrolidine hydrochlorideHCID 50908737HCID 50908737, 화합물

생성물 1

HCID 579502654-(Benzyloxy)-1-(9-methyl-2-(2-(pyrrolidin-1-yl)ethyl)-2,3,4,9,-tetrahydro-1h-pyrido[3,4-b]indol-7-yl)pyridine-2(1h)-one수율 7.7%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
65 °C

실험 절차

1-(2-Chloroethyl)pyrrolidine hydrochloride (50 mg, 0.29 mmol) was added to a solution of 4-(benzyloxy)-1-(9-methyl-2,3,4,9,-tetrahydro-1H-pyrido[3,4-b]indol-7-yl)pyridine-2(1H)-one (0.10 g, 0.27 mmol) and diisoproylethyl amine (0.14 mL) in EtOH (4 mL), and the resulting solution was heated at 65° C. for 2 h. The reaction mixture was concentrated to dryness under reduced pressure. Purification by flash column chromatography (40 g ISCO column, CH2Cl2/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 hold 5 column volumes increased to 0:100 over 20 column volumes) followed by preparative TLC (Analtech, 20×20 cm, 1000 microns, uV 254, 80:18:2 CH2Cl2/MeOH/NH4OH) followed by preparative HPLC (Phenomenex Luna C18 (2), 250.0×21.2 mm, 10 micron, H2O with 0.05% TFA and CH3CN with 0.05% TFA) and filtration through SCX-2 column gave the title compound (10 mg, 7%) as a yellow solid:

후처리

  1. concentrationThe reaction mixture was concentrated to dryness under reduced pressure
  2. customPurification
  3. temperatureby flash column chromatography (40 g ISCO column, CH2Cl2/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 hold 5 column volumes increased to 0:100 over 20 column volumes)
  4. filtrationfollowed by preparative HPLC (Phenomenex Luna C18 (2), 250.0×21.2 mm, 10 micron, H2O with 0.05% TFA and CH3CN with 0.05% TFA) and filtration through SCX-2 column

출처 및 근거

ORD 기록
ord-7d4002eb55f44c2e8741aaebab28122f
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08716308B2

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