Triethylamine hydrochloride → HCID 59287395, compound

HRID 1927225Notes

Reaction equation

HRID 1927225 reaction equation
[NH2:1][C:2]1[N:9]=[C:8]([CH2:10][O:11][CH3:12])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[N-:13]=[N+:14]=[N-:15].[Na+].Cl.C(N(CC)CC)C>CN1C(=O)CCC1>[CH3:12][O:11][CH2:10][C:8]1[N:9]=[C:2]([NH2:1])[C:3]([C:4]2[N:13]=[N:14][NH:15][N:5]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11130Triethylamine hydrochlorideHCID 33557Sodium AzideHCID 59287378HCID 59287378, compound

Product 1

HCID 59287395HCID 59287395, compoundYield 67.3%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
160 °C

Procedure

2-Amino-6-methoxymethyl-nicotinonitrile (0.20 g) described in Manufacturing Example 6-2, sodium azide (0.40 g), triethylamine hydrochloride (1.7 g), and NMP (25 mL) were stirred for 2 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:methanol=4:1) to obtain the titled compound (170 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:methanol=4:1)

Sources & evidence

ORD record
ord-0477054c7a9f481785574833ca88f8e6
Source dataset
uspto-grants-2012_05
Patent number
US08183264B2

Reaction notes

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