HCID 57435373, compound → HCID 57513765, compound

HRID 2368432Notes

Reaction equation

HRID 2368432 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[N:11][C:10]([NH2:20])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21]([O:28][C:29]1[O:30][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[N:33]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1(C)C=CC=CC=1>[CH2:21]([O:28][C:29](=[O:30])[NH:33][C:32]([C:31](=[O:36])[NH:20][C:10]1[N:11]=[C:12]([C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:9]=1)([CH3:34])[CH3:35])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 57435373HCID 57435373, compoundHCID 57435374HCID 57435374, compound

Product 1

HCID 57513765HCID 57513765, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

1-Benzyl-5-(4-fluorophenyl)-1H-1,2,4-triazol-3-amine (4.15 g, 15.47 mmol), 2-(benzyloxy)-4,4-dimethyloxazol-5(4H)-one (4.07 g, 18.56 mmol) were stirred in 5 ml of toluene in a 100 ml prbf. The white suspension was allowed to stir at 50° C. for over weekend. It was then cooled to r.t. The volatiles were removed in vacuo and the resulted solid was dissolved in EtOAc (130 mL) and heptane (50 mL) with heating. It was cooled to r.t. and let sit overnight. The resulted precipitates were collected and dried to afford the title compound. 1H NMR (400 MHz, DMSO-d6) 1.41 (s, 6H) 5.01 (s, 2H) 5.43 (s, 2H) 7.12 (d, J=6.82 Hz, 2H) 7.23-7.43 (m, 11H) 7.64-7.74 (m, 2H), 10.05 (br. s., 1H). MS (m/z) 488.1 M(+1), tR=1.60, Method A.

Workup

  1. temperatureIt was then cooled to r.t
  2. customThe volatiles were removed in vacuo
  3. dissolutionthe resulted solid was dissolved in EtOAc (130 mL)
  4. temperatureheptane (50 mL) with heating
  5. temperatureIt was cooled to r.t.
  6. customThe resulted precipitates
  7. customwere collected
  8. customdried

Sources & evidence

ORD record
ord-a2d049a160b546a8a45e00ceb765feab
Source dataset
uspto-grants-2014_04
Patent number
US08703761B2

Reaction notes

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