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Triethylamine → HCID 14371864, compound

HRID 1381948
Notes
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Reaction equation

HRID 1381948 reaction equation
Cl.[CH3:2][O:3][N:4]1[C:8](=[O:9])[CH2:7][C:6]2([CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[C:5]1=[O:15].[CH3:16][C:17]1[NH:18][C:19]([CH3:39])=[C:20]([C:35]([O:37][CH3:38])=[O:36])[CH:21]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-:34])=[O:33])[CH:27]=2)[C:22]=1[C:23](O)=[O:24].C(N(CC)CC)C.P(OC#N)(OCC)(OCC)=O>CN(C)C=O.O>[CH3:16][C:17]1[NH:18][C:19]([CH3:39])=[C:20]([C:35]([O:37][CH3:38])=[O:36])[CH:21]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([N+:32]([O-:34])=[O:33])[CH:27]=2)[C:22]=1[C:23]([N:12]1[CH2:13][CH2:14][C:6]2([C:5](=[O:15])[N:4]([O:3][CH3:2])[C:8](=[O:9])[CH2:7]2)[CH2:10][CH2:11]1)=[O:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 1733222,6-Dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid monomethyl esterHCID 30882852,8-Diazaspiro(4,5)decane-1,3-dione, 2-methoxy-, monohydrochlorideHCID 18315342HCID 18315342, compound

Product 1

HCID 14371864HCID 14371864, compoundYield 67.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of of 2-methoxy-2,8-diazaspiro[4,5]decane-1,3-dione.hydrochloride (0.21 g) obtained in Example 9, 1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)pyridine-3-carboxylic acid (0.3 g) and triethylamine (0.26 ml) in dimethylformamide (7 ml) was added dropwise, under ice-cooling, 0.22 ml of diethyl cyano phosphate, and the mixture was stirred for 30 minutes. To the reaction mixture was added water (20 ml), which was stirred at room temperature, followed by extraction with dichloromethane. The dichloromethane solution was dried over anhydrous sodium sulfate. The solvent was then evaporated off under reduced pressure. The residual oily product was subjected to a silica gel column chromatography (eluent, ethyl acetate), and the solvent for the solution containing the desired product was evaporated off under reduced pressure. The residual solid was recrystallized from ethanol to obtain 0.31 g of yellow crystals, m.p. 228° to 230° C.

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with dichloromethane
  3. dry with materialThe dichloromethane solution was dried over anhydrous sodium sulfate
  4. customThe solvent was then evaporated off under reduced pressure
  5. additionthe solvent for the solution containing the desired product
  6. customwas evaporated off under reduced pressure
  7. customThe residual solid was recrystallized from ethanol

Sources & evidence

ORD record
ord-b4b02d44d4b444d9839357b00232371c
Source dataset
uspto-grants-1989_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04804665

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes