Nicotinic Acid → HCID 68409913, compound

HRID 1511741Notes

Reaction equation

HRID 1511741 reaction equation
Cl.[C:2]1([O:12][CH:13]2[CH2:19][CH2:18][NH:17][CH2:16][C:15]3[O:20][C:21]([CH3:23])=[CH:22][C:14]2=3)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:31](O)(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[N:34][CH:33]=1.ON1C2C=CC=CC=2N=N1>C(Cl)Cl.O>[C:2]1([O:12][CH:13]2[CH2:19][CH2:18][N:17]([C:31]([C:32]3[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=3)=[O:38])[CH2:16][C:15]3[O:20][C:21]([CH3:23])=[CH:22][C:14]2=3)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 938Nicotinic AcidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 68410143HCID 68410143, compound

Product 1

HCID 68409913HCID 68409913, compoundYield 115.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

4-(Naphthalen-1-yloxy)-2-methyl-5,6,7,8-tetrahydro-4H-furo[2,3-c]azepine hydrochloride (50 mg) prepared in Example 284 and 47 mg of triethylamine were dissolved in 1 mL of methylene chloride, then 39 mg of 1-ethyl-3-(3-dimethyl-aminopropyl)carbodiimidehydrochloride (WSCD.HCl), 25 mg of nicotinic acid and 27 mg of 1-hydroxybenzotriazole were dropped thereinto successively and the mixture was stirred at room temperature for 6 hours. The reaction solution was poured over 2 mL of water and the mixture was subjected to extraction with methylene chloride. The organic layer was washed with water and a saturated solution of sodium chloride successively and dried over anhydrous magnesium sulfate and the solvent was evaporated therefrom in vacuo. The resulting residue was purified by silica gel column chromatography to give 70 mg of 4-(naphthalen-1-yloxy)-2-methyl-7-(3-pyridylcarbonyl)-5,6,7,8-tetrahydro-4H-furo[2,3-c]azepine.

Workup

  1. extractionthe mixture was subjected to extraction with methylene chloride
  2. washThe organic layer was washed with water
  3. dry with materiala saturated solution of sodium chloride successively and dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-455adfb0048c4ec4bd9e762cb9845568
Source dataset
uspto-grants-2012_07
Patent number
US08217031B2

Reaction notes

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