Triethylamine → 4-[2-(3-Nitro-phenyl)-oxazolo[4,5-b]pyridin-5-ylmethyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 419862Notes

Reaction equation

HRID 419862 reaction equation
Br[CH2:2][C:3]1[N:8]=[C:7]2[N:9]=[C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=3)[O:11][C:6]2=[CH:5][CH:4]=1.CCN(CC)CC.[C:28]([N:35]1[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]1)([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29]>CC#N>[C:31]([O:30][C:28]([N:35]1[CH2:40][CH2:39][N:38]([CH2:2][C:3]2[N:8]=[C:7]3[N:9]=[C:10]([C:12]4[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=4)[O:11][C:6]3=[CH:5][CH:4]=2)[CH2:37][CH2:36]1)=[O:29])([CH3:34])([CH3:32])[CH3:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 596800675-Bromomethyl-2-(3-nitro-phenyl)-oxazolo[4,5-b]pyridine

Product 1

HCID 596799094-[2-(3-Nitro-phenyl)-oxazolo[4,5-b]pyridin-5-ylmethyl]-piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Bromomethyl-2-(3-nitro-phenyl)-oxazolo[4,5-b]pyridine (250 mg, 0.75 mmol) was dissolved in 5 mL of CH3CN along with Et3N (0.200 mL, 1.5 mmol) and 140 mg of Boc-piperazine. The reaction mixture was stirred at room temperature for 18 hours. It was then concentrated and the resulting residue was mixed with 25 mL of CH2Cl2 and washed with brine. The organic layer was dried (Na2SO4) and concentrated to afford essentially quantitative yield of 4-[2-(3-nitro-phenyl)-oxazolo [4,5-b]pyridin-5-ylmethyl]-piperazine-1-carboxylic acid tert-butyl ester.

Workup

  1. concentrationIt was then concentrated
  2. additionthe resulting residue was mixed with 25 mL of CH2Cl2
  3. washwashed with brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2621b16f2b024f8f99031b8e52892345
Source dataset
uspto-grants-2012_01
Patent number
US08093401B2

Reaction notes

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