Water → N-(3-(3-bromopyridin-2-yloxy)cyclobutyl)benzo[d]thiazol-2-amine

HRID 1846770노트

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HRID 1846770 반응식
Cl.[Br: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][CH: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.O>CN1C(=O)CCC1>[Br: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][CH:8]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 119872-ChlorobenzothiazoleHCID 81531DiisopropylethylamineHCID 674787263-((3-Bromopyridin-2-yl)oxy)cyclobutanamine hydrochloride

생성물 1

HCID 58548561N-(3-(3-bromopyridin-2-yloxy)cyclobutyl)benzo[d]thiazol-2-amine수율 60%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
180 °C

실험 절차

A mixture of 3-((3-bromopyridin-2-yl)oxy)cyclobutanamine hydrochloride (242 mg, 1 mmol), 2-chloro-benzothiazole (169 mg, 1 mmol) and DIEA (286 mg, 2 mmol) in NMP (10 mL) was heated to 180° C. for 2 hours in microwave. The reaction mixture was added water, extracted with EtOAc (40 mL), washed with brine and dried over Na2SO4. The organic layers were concentrated and purified by column chromatography to give N-(3-((3-bromopyridin-2-yl)oxy)cyclobutyl)benzo[d]thiazol-2-amine (225 mg, 0.6 mmol, yield 60%). ESI-MS (M+1): 376 calc. for C16H14BrN3OS 375.

후처리

  1. extractionextracted with EtOAc (40 mL)
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationThe organic layers were concentrated
  5. custompurified by column chromatography

출처 및 근거

ORD 기록
ord-d646af6446424e1d8bb8d1728370f53e
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952037B2

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