Dimethylformamide → tert-Butyl (1-(5-bromotetrazolo[1,5-a]pyrazin-8-yl)azetidin-3-yl)(methyl)carbamate

HRID 535710Notes

Reaction equation

HRID 535710 reaction equation
[CH3:1][N:2]([CH:10]1[CH2:13][N:12]([C:14]2[C:15]3[N:16]([N:20]=[N:21][N:22]=3)[CH:17]=[CH:18][N:19]=2)[CH2:11]1)[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:7])[CH3:6].CN(C=O)C.[Br:28]N1C(=O)CCC1=O>O>[Br:28][C:17]1[N:16]2[N:20]=[N:21][N:22]=[C:15]2[C:14]([N:12]2[CH2:13][CH:10]([N:2]([CH3:1])[C:3](=[O:9])[O:4][C:5]([CH3:8])([CH3:6])[CH3:7])[CH2:11]2)=[N:19][CH:18]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67184N-bromobutanimideHCID 58446991HCID 58446991, compound

Product 1

HCID 58447038tert-Butyl (1-(5-bromotetrazolo[1,5-a]pyrazin-8-yl)azetidin-3-yl)(methyl)carbamateYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

A 3 L round bottom flask was charged with tert-butyl methyl(1-(tetrazolo[1,5-a]pyrazin-8-yl)azetidin-3-yl)carbamate (200 g, 0.66 mol) and DMF (1 L). To the above was added N-bromosuccinimide (117 g, 0.66 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 (500 mL), and dried to afford 200 g (79%) of the product as a white solid.

Workup

  1. filtrationThe resulting crystalline solid was collected by filtration
  2. washwashed with water (500 mL)
  3. customdried

Sources & evidence

ORD record
ord-67617714a014454995ab98fec4436420
Source dataset
uspto-grants-2014_10
Patent number
US08859550B2

Reaction notes

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