Triethylamine → HCID 18414408, compound

HRID 1978048Notes

Reaction equation

HRID 1978048 reaction equation
CC1[N:3]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][NH2:22])=[CH:16][CH:15]=3)[N:9]=2)C(C)=CC=1.[C:23]1([CH:29](C)[CH2:30][C:31](O)=O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[CH3:35]CN=C=NCCCN(C)C.ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.C([O-])(=O)CC(CC([O-])=O)(C([O-])=O)O>C(#N)C>[C:23]1([CH2:29][CH2:30][CH2:31][CH2:35][NH:22][CH2:21][CH2:20][C:17]2[CH:16]=[CH:15][C:14]([C:10]3[N:9]=[C:8]([NH2:3])[CH:13]=[CH:12][CH:11]=3)=[CH:19][CH:18]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 207243-Phenylbutyric acidHCID 31348CitrateHCID 757711-HydroxybenzotriazoleHCID 21995370HCID 21995370, compound

Product 1

HCID 18414408HCID 18414408, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 100 mL round-bottomed flask equipped with N2 inlet were added 200 mg (0.687 mmol) 2-(2,5-dimethylpyrrol-1-yl)-6-(4-(2-aminoethyl)phenyl)-pyridine (Example 100D), 113 mg (0.687 mmol) 3-phenylbutyric acid, 132 mg (0.687 mmol) EDAC, 10 mg N-hydroxybenzotriazole, 5 mL dry acetonitrile, and 211 uL (1.51 mmol) triethylamine. The reaction was stirred at room temperature for 12 h, poured into dilute aqueous citrate solution, and extracted into ethyl acetate. The organic layer was washed with water, aqueous sodium bicarbonate solution, and brine, dried over sodium sulfate, and evaporated. The resulting yellow oil, 300 mg (100%) was used directly.

Workup

  1. customTo a 100 mL round-bottomed flask equipped with N2 inlet
  2. extractionextracted into ethyl acetate
  3. washThe organic layer was washed with water, aqueous sodium bicarbonate solution, and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-07680c70c8fb49f685830bd9678b93ee
Source dataset
uspto-grants-2001_05
Patent number
US06235747B1

Reaction notes

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