Acetic Anhydride → N-(4,5,6,7-tetrahydro-5-(5,6-dimethoxypyrazin-2-yl)thiazolo[5,4-c]pyridin-2-yl)acetamide

HRID 39360노트

반응식

HRID 39360 반응식
[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]([N:11]2[CH2:16][CH2:15][C:14]3[N:17]=[C:18]([NH2:20])[S:19][C:13]=3[CH2:12]2)=[N:7][C:8]=1[O:9][CH3:10].CCN(C(C)C)C(C)C.[C:30](OC(=O)C)(=[O:32])[CH3:31]>C(Cl)Cl>[CH3:1][O:2][C:3]1[N:4]=[CH:5][C:6]([N:11]2[CH2:16][CH2:15][C:14]3[N:17]=[C:18]([NH:20][C:30](=[O:32])[CH3:31])[S:19][C:13]=3[CH2:12]2)=[N:7][C:8]=1[O:9][CH3:10]

참가 물질

5

반응물 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 866619525-(5,6-Dimethoxypyrazin-2-yl)-4,5,6,7-tetrahydrothiazolo[5,4-c]pyridin-2-amine

생성물 1

HCID 46872069N-(4,5,6,7-tetrahydro-5-(5,6-dimethoxypyrazin-2-yl)thiazolo[5,4-c]pyridin-2-yl)acetamide수율 49.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

As shown in step 9-vi of Scheme 9, to a solution of Compound 1032 (65.4 mg, 0.223 mmol) in DCM (2 mL) was added DIEA (200 μL, 1.148 mmol) and acetic anhydride (200 μL, 2.12 mmol). The reaction solution was stirred at room temperature for 150 min and the crude produce purified by medium pressure silica gel chromatography (10 to 80% EtOAc in Hexanes) to give N-(4,5,6,7-tetrahydro-5-(5,6-dimethoxypyrazin-2-yl)thiazolo[5,4-c]pyridin-2-yl)acetamide (Compound 14, 36.8 mg) as an off white solid, which was salted as its mono-mesylate salt to yield a beige solid: ESMS (M+H) 336.12; 1H NMR (300.0 MHz, DMSO-d6) δ 7.31 (s, 1H), 4.55 (s, 2H), 3.91 (m, 3H), 3.83 (m, 5H), 2.73 (t, J=5.4 Hz, 2H), 2.39 (d, J=0.6 Hz, 3H) and 2.12 (s, 3H) ppm.

후처리

  1. customthe crude produce
  2. custompurified by medium pressure silica gel chromatography (10 to 80% EtOAc in Hexanes)

출처 및 근거

ORD 기록
ord-0912db0cd489499ea55d404d14a6cb45
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524906B2

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