Hydrochloric Acid → HCID 16070401, compound

HRID 2240052Notes

Reaction equation

HRID 2240052 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][CH:34]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[O:15][CH2:16][CH2:17]Cl)[C:8]([S:19]([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])=[N:7]1.[CH3:35][NH2:36].Cl.CCOCC>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:32]=[CH:33][CH:34]=1)[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[O:15][CH2:16][CH2:17][NH:36][CH3:35])[C:8]([S:19]([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH:25]=[CH:24][CH:23]=2)(=[O:20])=[O:21])=[N:7]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 6329MethylamineHCID 59304172HCID 59304172, compound

Product 1

HCID 16070401HCID 16070401, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-(3-chloro-benzyl)-7-(2-chloro-ethoxy)-3-(naphthalene-1-sulfonyl)-1-H-indazole (0.065 g, 0.12 mmoles) and methylamine (0.48 mmoles) in DMF (1 mL) was stirred under nitrogen at 100° C. overnight. 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. The purified compound was dissolved in methanol, 1M HCl in ether (0.1 mL, 0.1 mmoles) was added, and compound was dried to afford the title compound as the HCl salt, MS: (ES+) 507 [M+H]+.

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
  7. dissolutionThe purified compound was dissolved in methanol
  8. customcompound was dried

Sources & evidence

ORD record
ord-4ab2e0939c614664a082cf305d6210a3
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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