2-Chlorobenzothiazole → N-(3-(3-chloropyrazin-2-yloxy)cyclobutyl)benzo[d]thiazol-2-amine

HRID 1846763노트

반응식

HRID 1846763 반응식
Cl.[Cl:2][C:3]1[C:4]([O:9][CH:10]2[CH2:13][CH:12]([NH2:14])[CH2:11]2)=[N:5][CH:6]=[CH:7][N:8]=1.Cl[C:16]1[S:17][C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[Cl:2][C:3]1[C:4]([O:9][CH:10]2[CH2:11][CH:12]([NH:14][C:16]3[S:17][C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[N:20]=3)[CH2:13]2)=[N:5][CH:6]=[CH:7][N:8]=1

참가 물질

5

반응물 3

HCID 119872-ChlorobenzothiazoleHCID 81531DiisopropylethylamineHCID 866601603-(3-Chloro-pyrazin-2-yloxy)-cyclobutylamine hydrochloride

생성물 1

HCID 58548522N-(3-(3-chloropyrazin-2-yloxy)cyclobutyl)benzo[d]thiazol-2-amine수율 95.5%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
180 °C

실험 절차

A mixture of 3-(3-chloro-pyrazin-2-yloxy)-cyclobutylamine hydrochloride (1.2 g, 6.28 mmol), 2-chloro-benzothiazole (purchased from ALDRICH™) (1.07 g, 6.28 mmol) and DIEA (1.8 g, 12.56 mmol) in NMP (12 mL) was heated to 180° C. for 2 hours in microwave. The reaction mixture was extracted with EtOAc (40 mL) and water, the organic phase was washed with brine and dried over Na2SO4. The organic layers were concentrated and purified by column chromatography on silica gel to give N-(3-((3-chloropyrazin-2-yl)oxy)cyclobutyl)benzo[d]thiazol-2-amine (3.0 g, 6 mmol, 95.5%). ESI-MS (M+1): 333 calc. for C15H13ClN4OS 332.

후처리

  1. extractionThe reaction mixture was extracted with EtOAc (40 mL) and water
  2. washthe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationThe organic layers were concentrated
  5. custompurified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-b37da26e7ec1446abda4dc122919990c
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952037B2

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