Ammonia → HCID 21906439, compound

HRID 1883009Notes

Reaction equation

HRID 1883009 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:32])[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]=[C:26]([C:30]#[N:31])[CH:25]=3)[CH2:20][CH2:19]2)=[N:6][CH:7]=1.CO.N.[SH2:36]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9](=[O:32])[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]=[C:26]([C:30](=[S:36])[NH2:31])[CH:25]=3)[CH2:20][CH2:19]2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 402Hydrogen SulfideHCID 887MethanolHCID 21906324HCID 21906324, compound

Product 1

HCID 21906439HCID 21906439, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A pressure tube was charged with N-(5-chloropyridin-2-yl)-2-[1-(2-cyanopyridin-4-yl)piperidin-4-ylmethylamino]-benzamide (50 mg, 0.11 mmol) and 1:2 methanol:tetrahydrofuran (3 mL); and the solution was treated with ammonia (g), sealed, and allowed to stir for 2 days. The mixture was then treated with hydrogen sulfide (g), sealed and allowed to stir for 2 days. The mixture was concentrated and the residue purified by column chromatography (SiO2: 2% methanol in methylene chloride) affording 38 mg (70%) of the title compound.

Workup

  1. customsealed
  2. customsealed
  3. stirringto stir for 2 days
  4. concentrationThe mixture was concentrated
  5. customthe residue purified by column chromatography (SiO2: 2% methanol in methylene chloride)

Sources & evidence

ORD record
ord-8b87af5827354b2d97e30615354fe9d5
Source dataset
uspto-grants-2004_07
Patent number
US06759414B2

Reaction notes

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