Diisopropylethylamine → 4-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]-1-[(2S)-2-hydroxypropanoyl]piperidine-4-carboxamide

HRID 1867727노트

반응식

HRID 1867727 반응식
CCN(C(C)C)C(C)C.[C:10]([OH:15])(=O)[C@H:11]([CH3:13])[OH:12].Cl.[Cl:17][C:18]1[C:19]([F:49])=[C:20]([NH:24][C:25]2[C:34]3[C:29](=[CH:30][C:31]([O:47][CH3:48])=[C:32]([CH2:35][N:36]([CH3:46])[C:37]4([C:43]([NH2:45])=[O:44])[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]4)[CH:33]=3)[N:28]=[CH:27][N:26]=2)[CH:21]=[CH:22][CH:23]=1>CN(C)C=O>[Cl:17][C:18]1[C:19]([F:49])=[C:20]([NH:24][C:25]2[C:34]3[C:29](=[CH:30][C:31]([O:47][CH3:48])=[C:32]([CH2:35][N:36]([CH3:46])[C:37]4([C:43]([NH2:45])=[O:44])[CH2:42][CH2:41][N:40]([C:10](=[O:15])[C@@H:11]([OH:12])[CH3:13])[CH2:39][CH2:38]4)[CH:33]=3)[N:28]=[CH:27][N:26]=2)[CH:21]=[CH:22][CH:23]=1

참가 물질

5

반응물 3

HCID 81531DiisopropylethylamineHCID 107689L-Lactic AcidHCID 690487244-[({4-[(3-Chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]piperidine-4-carboxamide hydrochloride

생성물 1

HCID 579798324-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]-1-[(2S)-2-hydroxypropanoyl]piperidine-4-carboxamide수율 43.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

DIPEA (0.120 g, 0.92 mmol) and L-lactic acid (0.083 g, 0.92 mmol) were added to a stirred solution of 4-[({4-[(3-chloro-2-fluorophenyl)amino]-7-methoxyquinazolin-6-yl}methyl)(methyl)amino]piperidine-4-carboxamide hydrochloride (0.10 g, 0.184 mmol) in dimethylformamide at room temperature. O-(1H-Benzotriazol-1-yl)-N,N,N′N′-tetramethyluronium tetrafluoroborate (0.295 g, 0.92 mmol) was added and the reaction mixture was stirred for 30 minutes, concentrated and purified by preparative LCMS (standard acidic system) to give the title product (0.044 g, 43.4%) as a white solid; 1H NMR Spectrum: (DMSO-d6) 1.29 (d, 3H), 1.91 (m, 2H), 2.06 (m, 2H), 2.20 (m, 3H), 3.34 (m, 4H), 3.65 (s, 2H), 3.94 (s, 3H), 4.45 (m, 1H), 4.83 (m, 1H), 7.19 (s, 1H), 7.29 (m, 3H), 7.49-7.57 (m, 2H), 8.34 (s, 1H), 8.42 (s, 1H), 9.73 (s, 1H); Mass Spectrum: (M+H)+ 545.

후처리

  1. concentrationconcentrated
  2. custompurified by preparative LCMS (standard acidic system)

출처 및 근거

ORD 기록
ord-d9df8cf4eb344b0c8e0e30a203054ca1
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07632840B2

반응 노트

불러오는 중…