Phenyl chloroformate → HCID 66833844, compound

HRID 1396019Notes

Reaction equation

HRID 1396019 reaction equation
[N:1]1[N:2]([C:6]2[N:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=2)[N:3]=[CH:4][CH:5]=1.Cl[C:14]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:15]>CC#N.CCOC(C)=O>[C:17]1([O:16][C:14](=[O:15])[NH:12][C:9]2[CH:10]=[N:11][C:6]([N:2]3[N:3]=[CH:4][CH:5]=[N:1]3)=[CH:7][CH:8]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 15891Phenyl chloroformateHCID 18071426949977-25-7

Product 1

HCID 66833844HCID 66833844, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution consisting of 6-[1,2,3]triazol-2-yl-pyridin-3-ylamine (1.00 g, 6.21 mmol) in CH3CN (10 mL) was added phenyl chloroformate (0.389 mL, 3.10 mmol) dropwise at rt. After 16 h, the reaction mixture was diluted with EtOAc (30 mL) and washed with saturated aq. NaCl. The organic layer was separated, dried (Na2SO4), and concentrated. The crude residue was purified (FCC) to give the title compound as a white solid (0.808 g, 93%). MS (ESI+): calcd. for C14H11N5O2, 281.09. m/z found, 282.1 (M+H)+.

Workup

  1. washwashed with saturated aq. NaCl
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe crude residue was purified (FCC)

Sources & evidence

ORD record
ord-a7086fcd93f5488abd02ac5b734c45da
Source dataset
uspto-grants-2014_12
Patent number
US08901111B2

Reaction notes

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