Sodium hydride → HCID 57343721, compound

HRID 2276897Notes

Reaction equation

HRID 2276897 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]([NH:23][CH:24]3[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]4C=CC([N+]([O-])=O)=C[CH:34]=4)=[O:31])[CH2:26][CH2:25]3)=[O:22])[C:9]=2[CH3:42])=[CH:4][CH:3]=1.[H-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=3[Cl:20])[N:11]=[C:10]([C:21]([NH:23][CH:24]3[CH2:25][CH2:26][N:27]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:28][CH2:29]3)=[O:22])[C:9]=2[CH3:42])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 86716054HCID 86716054, compound

Product 1

HCID 57343721HCID 57343721, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4-nitrophenyl 4-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-amido]piperidine-1-carboxylate (0.02 mmol, 1 eq.) and appropriate alcohol (0.5 mL) in THF (2 mL) was added sodium hydride 60% dispersion in mineral oil (4 mg, 0.1 mmol, 5 eq.). The reaction was stirred for 16 h and quenched with acetic acid. The reaction was concentrated in vacuo. The crude material was purified by column chromatography 0-100% ethyl acetate/hexanes to yield desired product.

Workup

  1. customquenched with acetic acid
  2. concentrationThe reaction was concentrated in vacuo
  3. customThe crude material was purified by column chromatography 0-100% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-144f67107e6446599ae70aa8f719c9c0
Source dataset
uspto-grants-2015_09
Patent number
US09133128B2

Reaction notes

Loading…