Triethylamine → HCID 69584822, compound

HRID 1743994Notes

Reaction equation

HRID 1743994 reaction equation
C(CC1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]2[N:20]=[C:19]([NH2:21])[CH:18]=[CH:17][CH:16]=2)=CC=1)(O)=O.[CH2:22]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C.ON1[C:48]2[CH:49]=[CH:50][CH:51]=C[C:47]=2N=N1.C[OH:54].C(Cl)Cl>C(#N)C>[C:24]1([CH2:23][CH2:22][N:30]2[CH2:31][CH2:32][N:33]([C:51]([C:50]3[C:14]4[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=4)[C:8]([C:15]4[N:20]=[C:19]([NH2:21])[CH:18]=[CH:17][CH:16]=4)=[C:48]([CH3:47])[CH:49]=3)=[O:54])[CH2:34][CH2:35]2)[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 792141-PhenethylpiperazineHCID 21226129Dichloromethane methanolHCID 22236426HCID 22236426, compound

Product 1

HCID 69584822HCID 69584822, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 100 mL round-bottomed flask equipped with condenser and N2 inlet were added 157 mg (0.50 mmol) 6-(4-carboxymethylnaphthalen-1-yl)-pyridin-2-ylamine, 95 mg (0.50 mmol) N-phenethylpiperazine, 96 mg (0.50 mmol) N-ethyl, N-3-dimethylaminopropyl-carbodiimide, 0.230 mL (1.65 mmol) triethylamine, 10 mg N-hydroxybenzotriazole, and 7 mL dry acetonitrile. The reaction was stirred at room temperature 12 hours (LCMS showed P+1=451 and TLC showed Rf=0.3 in 10% methanol/methylene chloride), then evaporated and the residue chromatographed on silica gel using methanol/methylene chloride as eluant to afford the product as a foam, 230 mg (˜100%).

Workup

  1. customTo a 100 mL round-bottomed flask equipped with condenser and N2 inlet
  2. customevaporated
  3. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-7e87a4da94004eb1961433b23d64ae00
Source dataset
uspto-grants-2006_03
Patent number
US07012078B2

Reaction notes

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