HCID 19089106, compound → HCID 19089103, compound

HRID 1463998Notes

Reaction equation

HRID 1463998 reaction equation
[CH3:1][Li].[C:3]([CH2:6][N:7]1[C:11]([NH:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=[N:8]1)([OH:5])=O>C(OCC)C.O1CCCC1>[C:3]([CH2:6][N:7]1[C:11]([NH:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH:9]=[N:8]1)(=[O:5])[CH3:1]

Participants

5

Reactant 2

HCID 19089106HCID 19089106, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 19089103HCID 19089103, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyllithium in diethyl ether (250 ml) was added to a solution of 1-carboxymethyl-5-triphenylmethylaminopyrazole (25.95 g) in tetrahydrofuran (400 ml) under ice-cooling and the mixture was stirred for 6 hours at ambient temperature. The reaction mixture was added to a mixture of ice-cold water (500 ml) and diethyl ether (500 ml). The organic layer was separated and dried over magnesium sulfate. The magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give 1-acetylmethyl-5-triphenylmethylaminopyrazole.

Workup

  1. temperaturecooling
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. filtrationThe magnesium sulfate was filtered off
  5. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-89f16bccd20c4467b36fb42abc55486b
Source dataset
uspto-grants-1994_04
Patent number
US05302712

Reaction notes

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