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

HRID 51853노트

반응식

HRID 51853 반응식
[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

참가 물질

4

반응물 2

HCID 24408BromineHCID 21303400HCID 21303400, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5d5c5f462ba04e849400f71ec41af09d
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713499B2

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