4-Azidophenacyl bromide → 2-Amino-5-(4-azidophenyl)imidazole-1-carboxylic acid tert-butyl ester

HRID 1468568Notes

Reaction equation

HRID 1468568 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10](=O)[CH2:11]Br)=[CH:6][CH:5]=1)=[N+:2]=[N-:3].[C:14]([NH:21][C:22]([NH2:24])=[NH:23])([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]>CN(C=O)C>[C:17]([O:16][C:14]([N:21]1[C:10]([C:7]2[CH:8]=[CH:9][C:4]([N:1]=[N+:2]=[N-:3])=[CH:5][CH:6]=2)=[CH:11][N:23]=[C:22]1[NH2:24])=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

4

Reactant 2

HCID 926274-Azidophenacyl bromideHCID 178454308HCID 178454308, compound

Product 1

HCID 579314382-Amino-5-(4-azidophenyl)imidazole-1-carboxylic acid tert-butyl esterYield 98.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(4-azidophenyl)-2-bromoethanone (1.50 g, 6.24 mmol) in anhydrous DMF (20 mL) was added Boc-guanidine (3.00 g, 18.7 mmol). The reaction was stirred at ambient temperature for 48 hours upon which the mixture was partitioned between EtOAc (150 mL) and water (75 mL). The organic layer was successively washed with water (3×50 mL) and brine (2×50 mL) before being dried (Na2SO4) and evaporated to dryness. The resulting crude oil was purified via flash column chromatography (10-50% EtOAc/Hexanes) to obtain the target 2-amino-5-(4-azidophenyl)imidazole-1-carboxylic acid tert-butyl ester (1.84 g, 58%) as a yellow solid: 1H NMR (300 MHz, DMSO-d6) δ 7.77 (d, 2H, J=8.1 Hz), 7.36 (s, 1H), 7.10 (dd, 2H, J=0.9, 8.1 Hz), 6.61 (br s, 2H), 1.58 (s, 9H); 13C NMR (75 MHz, DMSO-d6) δ 150.4, 148.9, 137.6, 136.2, 130.5, 126.2, 119.1, 106.2, 84.7, 27.5; HRMS (ESI) calcd for C8H6BrN3O (M+) 300.1335. found 300.1329.

Workup

  1. customwas partitioned between EtOAc (150 mL) and water (75 mL)
  2. washThe organic layer was successively washed with water (3×50 mL) and brine (2×50 mL)
  3. dry with materialbefore being dried (Na2SO4)
  4. customevaporated to dryness
  5. customThe resulting crude oil was purified via flash column chromatography (10-50% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-95db2e1efe9e4d00ad35b7d51f44c9c1
Source dataset
uspto-grants-2015_04
Patent number
US09005643B2

Reaction notes

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