Bromide ion → 2-Bromo-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepine

HRID 239097Notes

Reaction equation

HRID 239097 reaction equation
N(OC(C)(C)C)=O.[Br-:8].C(OC([N:16]1[CH2:22][CH2:21][C:20]2[S:23][C:24](N)=[N:25][C:19]=2[CH2:18][CH2:17]1)=O)(C)(C)C>C(#N)C>[Br:8][C:24]1[S:23][C:20]2[CH2:21][CH2:22][NH:16][CH2:17][CH2:18][C:19]=2[N:25]=1

Participants

5

Reactant 3

HCID 259Bromide ionHCID 10906Tert-Butyl nitriteHCID 84712457Tert-butyl 2-amino-4,5,7,8-tetrahydrothiazolo[5,4-d]azepine-6-carboxylate

Product 1

HCID 866864842-Bromo-5,6,7,8-tetrahydro-4H-thiazolo[4,5-d]azepine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

238 μl tert.-butyl nitrite was added to 447 mg cupper (II) bromide in 50 mL acetonitrile. The reaction was stirred 10 min. at RT and then 270 mg 2-amino-4,5,7,8-tetrahydro-thiazolo[4,5-d]-azepine-6-carboxylic acid tert-butyl ester was added. The reaction was stirred 30 min. at 60° C. The reaction was purified by HPLC. The residue was dissolved in 10 mL dichlormethane and 10 mL trifluor acetic acid and stirred at RT for 1 h. The mixture was evaporated to give 112 mg of the desired product. Rt: 0.92 min (method I), (M+H)+: 233/235

Workup

  1. stirringThe reaction was stirred 30 min. at 60° C
  2. customThe reaction was purified by HPLC
  3. dissolutionThe residue was dissolved in 10 mL dichlormethane
  4. stirring10 mL trifluor acetic acid and stirred at RT for 1 h
  5. customThe mixture was evaporated

Sources & evidence

ORD record
ord-1470513fd5de4268aafeba34a15090b7
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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