1,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamine → 6-[(Dimethylamino)methylene]-4,5,6,7-tetrahydro-1,4,4-trimethyl-7-oxo-1H-indazole-3-carboxylic acid ethyl ester

HRID 875096Notes

Reaction equation

HRID 875096 reaction equation
[CH3:1][N:2]1[C:10]2[C:9](=[O:11])[CH2:8][CH2:7][C:6]([CH3:13])([CH3:12])[C:5]=2[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N:3]1.C(O[CH:24](OC(C)(C)C)[N:25]([CH3:27])[CH3:26])(C)(C)C>CN(C)C=O>[CH3:24][N:25]([CH:27]=[C:8]1[C:9](=[O:11])[C:10]2[N:2]([CH3:1])[N:3]=[C:4]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:5]=2[C:6]([CH3:13])([CH3:12])[CH2:7]1)[CH3:26]

Participants

4

Reactant 2

HCID 5477121,1-bis(1,1-dimethylethoxy)-N,N,N-trimethylamineHCID 44235648Ethyl 1,4,4-trimethyl-7-oxo-4,5,6,7-tetrahydro-1H-indazole-3-carboxylate

Product 1

HCID 689343446-[(Dimethylamino)methylene]-4,5,6,7-tetrahydro-1,4,4-trimethyl-7-oxo-1H-indazole-3-carboxylic acid ethyl esterYield 87.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 1,4,4-trimethyl-7-oxo-4,5,6,7-tetrahydro-1H-indazole-3-carboxylate (4.8 g, 19.18 mmol) in anhydrous dimethylformamide (30 mL) was treated with dimethylformamide di-tert-butylacetal (9.19 mL, 38.35 mmol) at 65° C. for 2 hours. The mixture was evaporated to dryness and the crude material was crystallized from hexane to give the title compound (5.1 g, 87% yield).

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe crude material was crystallized from hexane

Sources & evidence

ORD record
ord-cb63e0a383d44ab19c163f4e5b6785ed
Source dataset
uspto-grants-2015_03
Patent number
US08981089B2

Reaction notes

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