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

HRID 1846770ノート

反応式

HRID 1846770 の反応式
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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
180 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d646af6446424e1d8bb8d1728370f53e
出典データセット
uspto-grants-2015_02
特許番号
US08952037B2

反応ノート

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