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2-Chloroethanol → 3-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]-1-(2-hydroxyethyl)azetidine-3-carboxamide

HRID 1867746
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HRID 1867746 반응식
[Cl:1][C:2]1[C:3]([F:31])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:29][CH3:30])=[C:16]([CH2:19][N:20]([CH3:28])[C:21]4([C:25]([NH2:27])=[O:26])[CH2:24][NH:23][CH2:22]4)[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1.C(N(C(C)C)CC)(C)C.Cl[CH2:42][CH2:43][OH:44].[I-].[K+]>C(#N)C>[Cl:1][C:2]1[C:3]([F:31])=[C:4]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][C:15]([O:29][CH3:30])=[C:16]([CH2:19][N:20]([CH3:28])[C:21]4([C:25]([NH2:27])=[O:26])[CH2:24][N:23]([CH2:42][CH2:43][OH:44])[CH2:22]4)[CH:17]=3)[N:12]=[CH:11][N:10]=2)[CH:5]=[CH:6][CH:7]=1
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참가 물질

6

반응물 4

HCID 342-ChloroethanolHCID 4875Potassium IodideHCID 81531DiisopropylethylamineHCID 579798103-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]azetidine-3-carboxamide

생성물 1

HCID 579798993-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]-1-(2-hydroxyethyl)azetidine-3-carboxamide수율 11%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of the hydrochloride salt of 3-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]azetidine-3-carboxamide (100 mg, 0.19 mmol Example 74), diisopropylethylamine (100 μl, 0.58 mmol), 2-chloroethanol (60 μl, 0.58 mmol) and potassium iodide (32 mg, 0.19 mmol) in acetonitrile (1.5 ml) was heated in a microwave at 160° C. for 20 minutes. Purification of the resulting product on preparative HPLC (standard basic condition) gave the title product (10 mg, 11%) as a white solid; 1H NMR Spectrum: (CDCl3) 2.40 (s, 3H), 2.75 (t, 2H), 3.47 (s, 2H), 3.61 (t, 2H), 3.70 (s, 2H), 3.93 (s, 3H), 3.93 (s, 2H), 5.41 (brs, 1H), 6.79 (brs, 1H), 7.18 (m, 2H), 7.21 (s, 1H), 7.75 (brs, 1H), 7.86 (s, 1H), 8.52 (brs, 1H), 8.74 (s, 1H); Mass Spectrum: (M+H)+ 489.

후처리

  1. customPurification of the resulting product on preparative HPLC (standard basic condition)

출처 및 근거

ORD 기록
ord-aaf11a5d895a417fb99d73211f8824b2
출처 데이터셋
uspto-grants-2009_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07632840B2

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