Ammonia → HCID 21906625, compound

HRID 1883010Notes

Reaction equation

HRID 1883010 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:34])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][CH2:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][C:25]=3C(OC)=O)[CH2:20][CH2:19]2)=[N:6][CH:7]=1.[NH3:35].[CH3:36][OH:37]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:34])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][CH2:17][CH:18]2[CH2:19][CH2:20][N:21]([C:24]3[CH:29]=[CH:28][N:27]=[C:26]([C:36](=[O:37])[NH2:35])[CH:25]=3)[CH2:22][CH2:23]2)=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 21906560HCID 21906560, compound

Product 1

HCID 21906625HCID 21906625, compoundYield 96%

Procedure

A pressure tube was charged with N-(5-chloropyridin-2-yl)-2-[[1-(3-methoxycarbonylpyridin-4-yl)piperidin-4-ylmethyl]amino]benzamide (50 mg, 0.10 mmol) and 2 N ammonia in methanol (5 mL), sealed, and placed in a 110° C. bath. After 4 h, the mixture was transfered to a 60° C. bath. After 3 days, the mixture was cooled, concentrated, and the residue purified by column chromatography (SiO2, 2% methanol in methylene chloride) affording 48 mg (96%) of the title compound.

Workup

  1. customsealed
  2. customplaced in a 110° C.
  3. customwas transfered to a 60° C.
  4. waitAfter 3 days
  5. temperaturethe mixture was cooled
  6. concentrationconcentrated
  7. customthe residue purified by column chromatography (SiO2, 2% methanol in methylene chloride)

Sources & evidence

ORD record
ord-2f32eedb9be3488488da1f35061e0064
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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