Ethyl isocyanate → (3S)-3-{[4-(4-bromo-2-fluorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl]methyl}-N-ethyl-1-pyrrolidinecarboxamide

HRID 2405439Notes

Reaction equation

HRID 2405439 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([CH2:14][C@@H:15]3[CH2:19][CH2:18][NH:17][CH2:16]3)=[N:12][NH:11][C:10]2=[O:20])=[C:5]([F:21])[CH:4]=1.O1CCCC1.C(N(CC)CC)C.[CH2:34]([N:36]=[C:37]=[O:38])[CH3:35]>O.ClCCl>[Br:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:10](=[O:20])[NH:11][N:12]=[C:13]2[CH2:14][C@@H:15]2[CH2:19][CH2:18][N:17]([C:37]([NH:36][CH2:34][CH3:35])=[O:38])[CH2:16]2)=[C:5]([F:21])[CH:4]=1

Participants

7

Reactant 4

HCID 8022Ethyl isocyanateHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 673755214-(4-bromo-2-fluorophenyl)-5-[(3S)-3-pyrrolidinylmethyl]-2,4-dihydro-3H-1,2,4-triazol-3-one hydrochloride

Product 1

HCID 67376184(3S)-3-{[4-(4-bromo-2-fluorophenyl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl]methyl}-N-ethyl-1-pyrrolidinecarboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Into a 4 mL vial was placed 4-(4-bromo-2-fluorophenyl)-5-[(3S)-3-pyrrolidinylmethyl]-2,4-dihydro-3H-1,2,4-triazol-3-one hydrochloride (0.212 mmol) and tetrahydrofuran (2 mL). In succession was added triethylamine (0.717 mmol) and ethyl isocyanate (0.253 mmol). The vial was capped and the solution stirred at room temperature for 1 h. The solution was poured into a 10 mL solution of 1:1 dichloromethane:water. The solution was shaken and allowed to settle. The organic layer was separated, dried over sodium sulfate, filtered, and concentrated in vacuo. No further purification was performed on the title compound (74 mg, 68%). MS(ES)+ m/e 412.2, 414.1 [M+H]+.

Workup

  1. customThe vial was capped
  2. stirringThe solution was shaken
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customNo further purification

Sources & evidence

ORD record
ord-8a060fbc86464a16bb542c7831378f6f
Source dataset
uspto-grants-2014_08
Patent number
US08802864B2

Reaction notes

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