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

HRID 1846763ノート

反応式

HRID 1846763 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

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-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.

後処理

  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

出典と根拠

ORDレコード
ord-b37da26e7ec1446abda4dc122919990c
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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