Triethylamine → 3,4,5,6-Tetrahydro-3,10-diazabenzo[e]azulene-1-carboxylic acid [1-(2-ethylaminoethyl)-2-oxo-1,2-dihydro-pyridin-3-yl]amide

HRID 481077Notes

Reaction equation

HRID 481077 reaction equation
OCC[O:4][C:5]1[C:10]([NH:11][C:12]([C:14]2[C:23]3[C:22]4[N:24]=[CH:25][CH:26]=[CH:27][C:21]=4[CH2:20][CH2:19][CH2:18][C:17]=3[NH:16][CH:15]=2)=[O:13])=[CH:9][CH:8]=[CH:7][N:6]=1.[CH2:28]([N:30](CC)[CH2:31][CH3:32])[CH3:29].CS(Cl)(=O)=O>C(Cl)Cl>[CH2:28]([NH:30][CH2:31][CH2:32][N:6]1[CH:7]=[CH:8][CH:9]=[C:10]([NH:11][C:12]([C:14]2[C:23]3[C:22]4[N:24]=[CH:25][CH:26]=[CH:27][C:21]=4[CH2:20][CH2:19][CH2:18][C:17]=3[NH:16][CH:15]=2)=[O:13])[C:5]1=[O:4])[CH3:29]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 206055903,4,5,6-Tetrahydro-3,10-diazabenzo[e]azulene-1-carboxylic acid [2-(2-hydroxy-ethoxy)pyridin-3-yl]amide

Product 1

HCID 700253733,4,5,6-Tetrahydro-3,10-diazabenzo[e]azulene-1-carboxylic acid [1-(2-ethylaminoethyl)-2-oxo-1,2-dihydro-pyridin-3-yl]amideYield 54.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 3,4,5,6-tetrahydro-3,10-diazabenzo[e]azulene-1-carboxylic acid [2-(2-hydroxy-ethoxy)pyridin-3-yl]amide (150 mg, 0.41 mmol) and triethylamine (125 mg, 1.2 mmol) in DCM (10 mL) at 0° C. is added methanesulfonyl chloride (94 mg, 0.82 mmol) dropwise. The mixture is stirred at 0° C. for 15 min. The solvent is removed and the residue is dissolved in acetonitrile (10 mL) and transferred to a sealed tube. Ethylamine (1 mL) is added and the mixture is heated at 60° C. for 3 h. The solvent is removed and the residue is separated by preparative TLC to give 87 mg of 3,4,5,6-tetrahydro-3,10-diazabenzo[e]azulene-1-carboxylic acid [1-(2-ethylaminoethyl)-2-oxo-1,2-dihydro-pyridin-3-yl]amide. LRMS Calcd 391.5; found M−1 390.2.

Workup

  1. customThe solvent is removed
  2. dissolutionthe residue is dissolved in acetonitrile (10 mL)
  3. customtransferred to a sealed tube
  4. additionEthylamine (1 mL) is added
  5. temperaturethe mixture is heated at 60° C. for 3 h
  6. customThe solvent is removed
  7. customthe residue is separated by preparative TLC

Sources & evidence

ORD record
ord-77165e8dfda24002a802cbeb49982c8b
Source dataset
uspto-grants-2003_11
Patent number
US06653471B2

Reaction notes

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