HCID 70896218, compound → HCID 70896188, compound

HRID 2369943Notes

Reaction equation

HRID 2369943 reaction equation
COC1C=CC(C[N:8]2[C:16]3=[CH:17][CH:18]=[N:19][C:20](=[O:21])[C:14]4=[C:15]3[C:10]([CH2:11][CH2:12][CH:13]4[CH2:22][CH:23]3[CH:28]4[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]4)[CH2:24]3)=[N:9]2)=CC=1>FC(F)(F)C(O)=O.CO>[N:25]12[CH2:30][CH2:29][CH:28]([CH2:27][CH2:26]1)[CH:23]([CH2:22][CH:13]1[CH2:12][CH2:11][C:10]3[C:15]4[C:16](=[CH:17][CH:18]=[N:19][C:20](=[O:21])[C:14]1=4)[NH:8][N:9]=3)[CH2:24]2

Participants

4

Reactant 1

HCID 70896218HCID 70896218, compound

Product 1

HCID 70896188HCID 70896188, compoundYield 88.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 2-(4-methoxybenzyl)-7-(quinuclidin-3-ylmethyl)-8,9-dihydro-2H-azepino[5,4,3-cd]indazol-6(7H)-one (219 mg, 0.51 mmol) in trifluoroacetic acid (3 mL) was subjected to microwave irradiation at 130° C. for 18 min. The mixture was diluted with methanol and concentrated in vacuo. The resulting residue was converted to the free base by elution through an SCX-2 cartridge and then purified by column chromatography (silica gel, (12%-100% solvent mixture B in methylene chloride; solvent mixture B=70:27:3 methylene chloride/methanol/concentrated ammonium hydroxide) to afford 7-(quinuclidin-3-ylmethyl)-8,9-dihydro-2H-azepino[5,4,3-cd]indazol-6(7H)-one (140 mg, 88%) as a colorless oil: MS (ESI+) m/z 311 (M+H).

Workup

  1. customirradiation at 130° C. for 18 min
  2. concentrationconcentrated in vacuo
  3. washThe resulting residue was converted to the free base by elution through an SCX-2 cartridge
  4. custompurified by column chromatography (silica gel, (12%-100% solvent mixture B in methylene chloride; solvent mixture B=70:27:3 methylene chloride/methanol/concentrated ammonium hydroxide)

Sources & evidence

ORD record
ord-c625fcfd2fde4c3aab003f28f9fa14dc
Source dataset
uspto-grants-2014_04
Patent number
US08710046B2

Reaction notes

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