Dimethylformamide → Tert-butyl 4-(5-bromotetrazolo[1,5-a]pyrazin-8-yl)piperazine-1-carboxylate

HRID 1045733Notes

Reaction equation

HRID 1045733 reaction equation
[N:1]1[N:2]=[N:3][N:4]2[CH:9]=[CH:8][N:7]=[C:6]([N:10]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]3)[C:5]=12.CN(C=O)C.[Br:28]N1C(=O)CCC1=O>O>[Br:28][C:9]1[N:4]2[N:3]=[N:2][N:1]=[C:5]2[C:6]([N:10]2[CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][CH2:15]2)=[N:7][CH:8]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 58447015Tert-butyl 4-(tetrazolo[1,5-a]pyrazin-8-yl)piperazine-1-carboxylate

Product 1

HCID 58447025Tert-butyl 4-(5-bromotetrazolo[1,5-a]pyrazin-8-yl)piperazine-1-carboxylateYield 81.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

A 3 L round bottom flask was charged with tert-butyl 4-(tetrazolo[1,5-a]pyrazin-8-yl)piperazine-1-carboxylate (500 g, 1.6 mol) and DMF (2 L). To the above was added N-bromosuccinimide (320 g, 1.8 mol) in portions at 10° C. The resulting mixture was stirred at 10° C. for 0.5 h. Work-up: the reaction mixture was poured into water (3 L). The resulting crystalline solid was collected by filtration, washed with water (300 mL), and dried to afford 500 g (79%) of the product as a red solid. MS m/z: 384 (M+H+).

Workup

  1. filtrationThe resulting crystalline solid was collected by filtration
  2. washwashed with water (300 mL)
  3. customdried

Sources & evidence

ORD record
ord-7a622d29b80d40af86bead0e96483169
Source dataset
uspto-grants-2013_10
Patent number
US08569300B2

Reaction notes

Loading…