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

HRID 51853Notes

Reaction equation

HRID 51853 reaction equation
[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

Participants

4

Reactant 2

HCID 24408BromineHCID 21303400HCID 21303400, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-5d5c5f462ba04e849400f71ec41af09d
Source dataset
uspto-grants-2004_03
Patent number
US06713499B2

Reaction notes

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