Isopropylamine → HCID 178456797, compound

HRID 2205401Notes

Reaction equation

HRID 2205401 reaction equation
O([C:8]1[C:13]([C:14]2[N:18]=[CH:17][NH:16][N:15]=2)=[N:12][N:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:10](=[O:25])[CH:9]=1)C1C=CC=CC=1.[CH:26]([NH2:29])([CH3:28])[CH3:27]>CCO>[CH:26]([NH:29][C:8]1[C:13]([C:14]2[N:18]=[CH:17][NH:16][N:15]=2)=[N:12][N:11]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:10](=[O:25])[CH:9]=1)([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 178516552HCID 178516552, compound

Product 1

HCID 178456797HCID 178456797, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

5-Phenoxy-2-phenyl-6-(1H-1,2,4-triazol-3-yl)-3(2H)-pyridazinone (see Example 8) (140 mg, 0.42 mmol), isopropylamine (355 mg, 6 mmol) and EtOH (4 mL) were placed in a 10 mL pressurized reaction vial. The mixture was heated by microwave irradiation at 150° C. for 60 min. The solvent was then evaporated off and the residue was crystallized on treatment with Et2O (15 mL). The crude product was filtered off and recrystallized from a 3:2 mixture of EtOH and Et2O (10 mL) to yield a white crystalline substance (94 mg, 76%). Mp 203-205° C., 1H NMR (400 MHz, DMSO-d6) δ 1.27 (d, 6H, J=6.3 Hz, CH3), 3.71-3.77 (m, 1H, CH(CH3)2), 5.83 (s, 1H, H-4), 7.37-7.66 (m, 5H, C6H5), 8.32 (br s, 1H), 8.46 (br s, 1H) ppm.

Workup

  1. customreaction vial
  2. customThe solvent was then evaporated off
  3. customthe residue was crystallized on treatment with Et2O (15 mL)
  4. filtrationThe crude product was filtered off
  5. customrecrystallized from a 3:2 mixture of EtOH and Et2O (10 mL)
  6. customto yield a white crystalline substance (94 mg, 76%)

Sources & evidence

ORD record
ord-f471a53fe55d44e9a43ca368cd2352a8
Source dataset
uspto-grants-2016_06
Patent number
US09371290B2

Reaction notes

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