Triethylamine → tert-Butyl 3-(4-(6-Bromo-4-methyl-3-oxo-3,4-dihydropyrazin-2-ylamino)phenyl)azetidine-1-carboxylate

HRID 1919097Notes

Reaction equation

HRID 1919097 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9]2)=[CH:4][CH:3]=1.Br[C:20]1[C:21](=[O:28])[N:22]([CH3:27])[CH:23]=[C:24]([Br:26])[N:25]=1.C(N(CC)CC)C>C(O)(C)C>[Br:26][C:24]1[N:25]=[C:20]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH:8]3[CH2:9][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:11]3)=[CH:6][CH:7]=2)[C:21](=[O:28])[N:22]([CH3:27])[CH:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 130629693,5-Dibromo-1-methyl-1H-pyrazin-2-oneHCID 56956222tert-Butyl 3-(4-aminophenyl)azetidine-1-carboxylate

Product 1

HCID 58044293tert-Butyl 3-(4-(6-Bromo-4-methyl-3-oxo-3,4-dihydropyrazin-2-ylamino)phenyl)azetidine-1-carboxylateYield 78.5%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 298a (500 mg, 2.02 mmol), 3,5-dibromo-1-methylpyrazin-2(1H)-one (536 mg, 2.02 mmol) and triethylamine (0.6 mL, 4.04 mmol) in isopropanol (10 mL) was heated at reflux for 4 days. The solvent was evaporated in vacuo and the residue was purified on reverse phase Combi-flash to afford 298b (690 mg, 66%). MS: [M+H]+ 435.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 days
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was purified on reverse phase Combi-flash

Sources & evidence

ORD record
ord-a2928559912c4e8782ecc62b6348c408
Source dataset
uspto-grants-2013_12
Patent number
US08618107B2

Reaction notes

Loading…