2-Chlorobenzothiazole → HCID 178454112、化合物

HRID 707263ノート

反応式

HRID 707263 の反応式
[C:1]([O:5][C:6](=[O:13])[NH:7][C@H:8]1[CH2:11][C@@H:10]([NH2:12])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Cl[C:15]1[S:16][C:17]2[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=2[N:19]=1.C(N(CC)C(C)C)(C)C>CS(C)=O.O>[C:1]([O:5][C:6](=[O:13])[NH:7][C@H:8]1[CH2:11][C@@H:10]([NH:12][C:15]2[S:16][C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=3[N:19]=2)[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 3

HCID 119872-ChlorobenzothiazoleHCID 81531DiisopropylethylamineHCID 178454110HCID 178454110、化合物

生成物 1

HCID 178454112HCID 178454112、化合物収率 69.4%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
110 °C

実験手順

A mixture of tert-butyl(cis-3-aminocyclobutyl)carbamate (1.26 g, 6.77 mmol), 2-chlorobenzothiazole (0.965 mL, 6.77 mmol) and N,N-diisopropylethylamine (2.354 mL, 13.53 mmol) in DMSO (5 mL) was heated to 110° C. in a sealed microwave vial for 4 h, cooled to room temperature, diluted with water and extracted with EtOAc. EtOAc extract was concentrated and crude material purified with ISCO using silica gel column eluting with 0-80% EtOAc/hexane to give the desired product tert-butyl(cis-3-(benzo[d]thiazol-2-ylamino)cyclobutyl)carbamate (1.5 g, 4.70 mmol, 69.4% yield). m/z: 320.1 (M+1).

後処理

  1. temperaturecooled to room temperature
  2. extractionextracted with EtOAc
  3. extractionEtOAc extract
  4. concentrationwas concentrated
  5. customcrude material purified with ISCO
  6. washeluting with 0-80% EtOAc/hexane

出典と根拠

ORDレコード
ord-7e8bb65403b54011a99136f7c119d068
出典データセット
uspto-grants-2015_11
特許番号
US09174992B2

反応ノート

読み込み中…