Ammonium Chloride → HCID 178482247, compound

HRID 2233857Notes

Reaction equation

HRID 2233857 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[NH4+].[Cl-].[Cl:7][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([N:16]2[CH2:21][CH2:20][CH:19]([NH:22][CH3:23])[CH2:18][CH2:17]2)[N:15]=1)[C:11]#[N:12]>CN(C=O)C>[Cl:7][C:8]1[N:15]=[C:14]([N:16]2[CH2:21][CH2:20][CH:19]([NH:22][CH3:23])[CH2:18][CH2:17]2)[CH:13]=[C:10]([C:11]2[NH:12][N:3]=[N:2][N:1]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 860383832-Chloro-6-[4-(methylamino)piperidin-1-yl]isonicotinonitrile2×

Product 1

HCID 178482247HCID 178482247, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Sodium azide (131 mg, 2.02 mmol) and NH4Cl (108 mg, 2.02 mmol) were added to a solution of 2-chloro-6-[4-(methylamino)piperidin-1-yl]isonicotinonitrile (Intermediate 63, 507 mg, 2.02 mmol) in anhydrous DMF (3 ml). The mixture was heated at 120° C. under nitrogen gas for 1 h where LCMS showed the expected mass. The mixture was filtered and was purified by semi-preparative HPLC eluting with acetonitrile/water (0.1% TFA) and the title compound was concentrated in vacuo to give a hygroscopic brown solid (220 mg).

Workup

  1. filtrationThe mixture was filtered
  2. customwas purified by semi-preparative HPLC
  3. washeluting with acetonitrile/water (0.1% TFA)
  4. concentrationthe title compound was concentrated in vacuo

Sources & evidence

ORD record
ord-08f0d26f503747cc989ca118c020fe52
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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