Isopropanol → HCID 11200784, compound

HRID 2054424Notes

Reaction equation

HRID 2054424 reaction equation
Cl[C:2]1[N:7]2[N:8]=[C:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[C:10]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][CH:12]=3)=[C:6]2[N:5]=[C:4]([CH3:25])[N:3]=1.C([O-])(O)=O.[Na+].[CH:31]([OH:34])([CH3:33])[CH3:32]>>[Cl:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:9]1[C:10]([C:11]2[CH:12]=[CH:13][C:14]([Cl:17])=[CH:15][CH:16]=2)=[C:6]2[N:5]=[C:4]([CH3:25])[N:3]=[C:2]([O:34][CH:31]([CH3:33])[CH3:32])[N:7]2[N:8]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 516892Sodium BicarbonateHCID 59655729HCID 59655729, compound

Product 1

HCID 11200784HCID 11200784, compound

Conditions

Temperature
80 °C

Procedure

To a suspension of 4-chloro-7-(2-chlorophenyl)-8-(4-chlorophenyl)-2-methylpyrazolo[1,5-a][1,3,5]triazine (I-2A-1b; 150 mg, 0.384 mmol) in isopropanol (5 ml) was added solid NaHCO3 (129 mg, 1.5 mmol), and the mixture was heated at 80° C. overnight. After cooling, the suspended solids (150 mg) were collected by filtration and the filtrate was concentrated, in vacuo, to give a solid (95 mg). The suspended solids were extracted from saturated aqueous NaHCO3 with ethyl acetate, the organic layers were dried (MgSO4) and then concentrated, in vacuo, to give a solid. The combined solids were then purified on a Biotage™ Flash 12M column using 0-10% ethyl acetate in hexanes to afford 13A-1 (91 mg, 60%) as an off-white solid: +ESI MS (M+1) 413.4; 1H NMR (400 MHz, CD2Cl2) δ 7.50-7.34 (m, 6H), 7.24 (d, J=8.7 Hz, 2H), 5.73 (septuplet, J=6.2 Hz, 1H), 2.62 (s, 3H), 1.55 (d, J=6.2 Hz, 6H).

Workup

  1. temperatureAfter cooling
  2. filtrationthe suspended solids (150 mg) were collected by filtration
  3. concentrationthe filtrate was concentrated, in vacuo

Sources & evidence

ORD record
ord-3e4e6968d2e64f6f8e79d8d2f2b68825
Source dataset
uspto-grants-2008_02
Patent number
US07329658B2

Reaction notes

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