Ethanol → HCID 59655725, compound

HRID 2054423Notes

Reaction equation

HRID 2054423 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.[H-].[Na+].[CH2:28]([OH:30])[CH3:29]>>[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:30][CH2:28][CH3:29])[N:7]2[N:8]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24758Sodium hydrideHCID 59655729HCID 59655729, compound

Product 1

HCID 59655725HCID 59655725, compound

Procedure

To a solution of 4-chloro-7-(2-chlorophenyl)-8-(4-chlorophenyl)-2-methylpyrazolo[1,5-a][1,3,5]triazine (I-2A-1b; 20 mg, 0.051 mmol) in ethanol (1 ml) was added NaH (60% dispersion in oil, 2 mg, 0.05 mmol), portionwise. After stirring for 6 hours, the reaction was concentrated, in vacuo. The residue was redisolved in methylene chloride, filtered through a 0.45 μm disk, and then concentrated to afford 12A-1 (18 mg, 88%) as a solid: +APcI MS (M+1) 399.1; 1H NMR (400 MHz, CD2Cl2) δ 7.50-7.37 (m, 6H), 7.24 (d, J=8.7 Hz, 2H), 4.80 (q, J=7.2 Hz, 2H), 2.63 (s, 3H), 1.57 (t, J=7.1 Hz, 3H).

Workup

  1. concentrationthe reaction was concentrated, in vacuo
  2. filtrationfiltered through a 0.45 μm disk
  3. concentrationconcentrated
  4. customto afford 12A-1 (18 mg, 88%) as a solid

Sources & evidence

ORD record
ord-8dc7d37fa53e4979b2d02f444615b71a
Source dataset
uspto-grants-2008_02
Patent number
US07329658B2

Reaction notes

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