Triethylamine hydrochloride → HCID 59287388, compound

HRID 1927229Notes

Reaction equation

HRID 1927229 reaction equation
[NH2:1][C:2]1[N:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[N-:11]=[N+:12]=[N-:13].[Na+].Cl.C(N(CC)CC)C>CN1C(=O)CCC1>[NH3:1].[N:5]1[NH:11][N:12]=[N:13][C:4]=1[C:3]1[C:2]([NH2:1])=[N:9][C:8]([NH2:10])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 218881622,6-Diaminopyridine-3-carbonitrile

Product 2

HCID 222AmmoniaHCID 59287388HCID 59287388, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

2,6-Diamino-nicotinonitrile (0.50 g) described in Manufacturing Example 7-2, sodium azide (1.2 g), triethylamine hydrochloride (5.1 g), and NMP (45 mL) were stirred for 11 hours at 160° C. The reaction solution was directly purified by silica gel chromatography (ethyl acetate, then ethyl acetate:methanol:concentrated aqueous ammonia=6:2:1). The organic layer thus obtained was concentrated and purified by silica gel chromatography (ethyl acetate, then ethyl acetate:methanol=4:1, then ethyl acetate:methanol:concentrated aqueous ammonia=6:2:1) to obtain the titled compound (270 mg).

Workup

  1. customThe reaction solution was directly purified by silica gel chromatography (ethyl acetate
  2. customThe organic layer thus obtained
  3. concentrationwas concentrated
  4. custompurified by silica gel chromatography (ethyl acetate

Sources & evidence

ORD record
ord-46a78159f71f492884639eb07105a79d
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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