Bromine → 4-methoxy-7-{(1S,4S)-(2-oxa-5-aza-bicyclo[2.2.1]hept-5-yl)}-benzothiazol-2-ylamine

HRID 51853ノート

反応式

HRID 51853 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][C@@H:13]3[CH2:15][C@H:10]2[CH2:11][O:12]3)=[CH:5][C:4]=1[NH:16][C:17]([NH2:19])=[S:18].BrBr>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]2[N:16]=[C:17]([NH2:19])[S:18][C:5]=2[C:6]([N:9]2[CH2:14][C@@H:13]3[CH2:15][C@H:10]2[CH2:11][O:12]3)=[CH:7][CH:8]=1

参加物

4

反応物 2

HCID 24408BromineHCID 21303400HCID 21303400、化合物

生成物 1

HCID 213034014-methoxy-7-{(1S,4S)-(2-oxa-5-aza-bicyclo[2.2.1]hept-5-yl)}-benzothiazol-2-ylamine収率 33%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

To a stirred solution of 279 mg (1.00 mmol) [2-methoxy-5-{(1S,4S)-(2-oxa-5-aza-bicyclo[2.2.1]hept-5-yl)}-phenyl]-thiourea in 8 ml chloroform at room temperature was added dropwise 0.051 ml (1.00 mmol) bromine and the mixture heated at reflux for 24 h. The mixture was then concentrated in vacuo and the residue suspended in water. Sodium bicarbonate solution was added until the pH was 10, and the crystals were collected by filtration. Flash chromatography (5/95 methanol/dichloromethane) afforded 91.5 mg (33%) 4-methoxy-7-{(1S,4S)-(2-oxa-5-aza-bicyclo[2.2.1]hept-5-yl)}-benzothiazol-2-ylamine as an off-white crystalline solid. ES-MS m/e (%): 278 (M+H+, 100).

後処理

  1. temperaturethe mixture heated
  2. temperatureat reflux for 24 h
  3. concentrationThe mixture was then concentrated in vacuo
  4. additionSodium bicarbonate solution was added until the pH was 10
  5. filtrationthe crystals were collected by filtration

出典と根拠

ORDレコード
ord-5d5c5f462ba04e849400f71ec41af09d
出典データセット
uspto-grants-2004_03
特許番号
US06713499B2

反応ノート

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