p-Toluenesulfonic acid monohydrate → 3,4,5,6-Tetrahydro-3,10-diazabenzo[e]azulene-1-carboxylic acid [2-(2-hydroxy-ethoxy)pyridin-3-yl]amide

HRID 481076Notes

Reaction equation

HRID 481076 reaction equation
O1CCCCC1[O:7][CH2:8][CH2:9][O:10][C:11]1[C:16]([NH:17][C:18]([C:20]2[C:29]3[C:28]4[N:30]=[CH:31][CH:32]=[CH:33][C:27]=4[CH2:26][CH2:25][CH2:24][C:23]=3[NH:22][CH:21]=2)=[O:19])=[CH:15][CH:14]=[CH:13][N:12]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:7][CH2:8][CH2:9][O:10][C:11]1[C:16]([NH:17][C:18]([C:20]2[C:29]3[C:28]4[N:30]=[CH:31][CH:32]=[CH:33][C:27]=4[CH2:26][CH2:25][CH2:24][C:23]=3[NH:22][CH:21]=2)=[O:19])=[CH:15][CH:14]=[CH:13][N:12]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 865883163,4,5,6-Tetrahydro-3,10-diaza-benzo[e]azulene-1-carboxylic acid {2-[2-(tetrahydropyran-2-yloxy)-ethoxy]-pyridin-3-yl}amide

Product 1

HCID 206055903,4,5,6-Tetrahydro-3,10-diazabenzo[e]azulene-1-carboxylic acid [2-(2-hydroxy-ethoxy)pyridin-3-yl]amideYield 101.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3,4,5,6-tetrahydro-3,10-diaza-benzo[e]azulene-1-carboxylic acid {2-[2-(tetrahydropyran-2-yloxy)-ethoxy]-pyridin-3-yl}amide (850 mg) and p-toluenesulfonic acid monohydrate (700 mg) in methanol (30 mL) is refluxed for 1 h. The solvent is removed and the residue is extracted with DCM and washed with NaHCO3 (aq.). The organic layer is dried and solvent removed to give 700 mg of 3,4,5,6-tetrahydro-3,10-diazabenzo[e]azulene-1-carboxylic acid [2-(2-hydroxy-ethoxy)pyridin-3-yl]amide.

Workup

  1. customThe solvent is removed
  2. extractionthe residue is extracted with DCM
  3. washwashed with NaHCO3 (aq.)
  4. customThe organic layer is dried
  5. customsolvent removed

Sources & evidence

ORD record
ord-cd8cf214f89a4df7a6e75aaa1d6cc74a
Source dataset
uspto-grants-2003_11
Patent number
US06653471B2

Reaction notes

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