Triethylamine → (S)-N-(1-(8-chloro-1-(2-morpholinoethyl)isoquinolin-3-yl)ethyl)thiazolo[5,4-d]pyrimidin-7-amine

HRID 1051789노트

반응식

HRID 1051789 반응식
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)=[N:9][C:8]([C@@H:20]([NH2:22])[CH3:21])=[CH:7]2.Cl[C:24]1[C:25]2[N:32]=[CH:31][S:30][C:26]=2[N:27]=[CH:28][N:29]=1.C(N(CC)CC)C>CCCCO>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10]([CH2:12][CH2:13][N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)=[N:9][C:8]([C@@H:20]([NH:22][C:24]1[C:25]3[N:32]=[CH:31][S:30][C:26]=3[N:27]=[CH:28][N:29]=1)[CH3:21])=[CH:7]2

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 2630077-Chlorothiazolo[5,4-D]pyrimidineHCID 68747373(S)-1-(8-chloro-1-(2-morpholinoethyl)isoquinolin-3-yl)ethanamine

생성물 1

HCID 57330000(S)-N-(1-(8-chloro-1-(2-morpholinoethyl)isoquinolin-3-yl)ethyl)thiazolo[5,4-d]pyrimidin-7-amine

시약·촉매·용매 1

HCID 2631-Butanol용매

실험 절차

A mixture of (S)-1-(8-chloro-1-(2-morpholinoethyl)isoquinolin-3-yl)ethanamine 71 (100 mg, 0.31 mmol, 1 eq), 7-chlorothiazolo[5,4-d]pyrimidine (E-4) (108 mg, 0.63 mmol, 2 eq) and triethylamine (130 mg, 1.25 mmol, 4.0 eq) in n-BuOH (40 mL) was stirred at reflux for 16 h. The reaction mixture was cooled to RT and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel (1-5% MeOH-DCM) to afford the product (S)—N-(1-(8-chloro-1-(2-morpholinoethyl)isoquinolin-3-yl)ethyl)thiazolo[5,4-d]pyrimidin-7-amine 72. ESI-MS m/z: 455.0 [M+H]+.

후처리

  1. temperatureat reflux for 16 h
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by flash column chromatography on silica gel (1-5% MeOH-DCM)

출처 및 근거

ORD 기록
ord-e7dbf36e70374092a4d8acb20faf7463
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09388183B2

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