Dimethylamine → HCID 68679207, compound

HRID 2240092Notes

Reaction equation

HRID 2240092 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][CH:35]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([CH2:15][O:16][CH2:17][CH2:18]Cl)=[CH:12][CH:13]=2)[C:8]([S:20]([C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][CH:24]=2)(=[O:22])=[O:21])=[N:7]1.[CH3:36][NH:37][CH3:38]>CS(C)=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:33]=[CH:34][CH:35]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([CH2:15][O:16][CH2:17][CH2:18][N:37]([CH3:38])[CH3:36])=[CH:12][CH:13]=2)[C:8]([S:20]([C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=[CH:25][CH:24]=2)(=[O:21])=[O:22])=[N:7]1

Participants

5

Reactant 2

HCID 674DimethylamineHCID 68704610HCID 68704610, compound

Product 1

HCID 68679207HCID 68679207, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(3-chlorobenzyl)-5-(2-chloroethoxymethy)-3-(1-naphthylsulfony)-1H-indazole (0.08 g, 0.16 mmoles) and dimethylamine (0.28 ml, 0.56 mmoles) in DMSO (1 mL) was stirred under nitrogen at 100° C. for 4 hours. Mixture was cooled to room temperature, diluted with water, extracted with EtOAc, washed with water (2×), brine (1×), dried over Na2SO4, and concentrated under vacuum. Compound was purified by flash chromatography using as eluent 5% CH3OH/EtOAc to afford the title compound (0.08 g, 0.15 mmoles).

Workup

  1. temperatureMixture was cooled to room temperature
  2. extractionextracted with EtOAc
  3. washwashed with water (2×), brine (1×)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum
  6. customCompound was purified by flash chromatography

Sources & evidence

ORD record
ord-7f13c5742ef244f5a06f38c22f02b25d
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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