Hydrochloric Acid → HCID 10232531, compound

HRID 1727946Notes

Reaction equation

HRID 1727946 reaction equation
[OH-:1].[Na+].[CH:3]1[C:13]2[CH:12]=[CH:11][C:10]3[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=3[CH:8]([CH2:18][CH2:19]OC(C3C(C4C=CC=C(Cl)C=4)C(C(OCCC#N)=O)=C(C)NC=3C)=O)[C:7]=2[CH:6]=[CH:5][CH:4]=1.[ClH:45].CCN=C=N[CH2:51][CH2:52][CH2:53]N(C)C.Cl.[CH3:58][N:59]1[CH2:64][CH2:63][NH:62][CH2:61][CH2:60]1.C([N:67]([CH2:70][CH3:71])[CH2:68][CH3:69])C.CN([C:75]1[CH:80]=[CH:79][CH:78]=[CH:77]N=1)C.F[C:82](F)(F)[C:83]([O-:85])=[O:84].[CH3:88]O>ClCCl>[CH:14]1[C:10]2[CH:11]=[CH:12][C:13]3[CH:3]=[CH:4][CH:5]=[CH:6][C:7]=3[CH:8]([CH2:18][CH2:19][O:85][C:83](=[O:84])[C:82]3[C:78]([C:79]4[CH:53]=[CH:52][CH:51]=[C:75]([Cl:45])[CH:80]=4)=[C:77]([C:58]([N:59]4[CH2:64][CH2:63][N:62]([CH3:88])[CH2:61][CH2:60]4)=[O:1])[C:68]([CH3:69])=[N:67][C:70]=3[CH3:71])[C:9]=2[CH:17]=[CH:16][CH:15]=1

Participants

11

Reactant 9

HCID 313Hydrochloric AcidHCID 887Methanol2×HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 218852-DimethylaminopyridineHCID 531671-MethylpiperazineHCID 84468TrifluoroacetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 69070218HCID 69070218, compound

Product 1

HCID 10232531HCID 10232531, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4 ml of methanol and 0.32 ml of 1 N aqueous sodium hydroxide solution were added to 153 mg (0.265 mmol) of 4-(3-chlorophenyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-cyanoethyl) ester 5-(2-(5H-dibenzo[a,d] cyclohepten-5-yl) ethyl) ester and stirred at room temperature overnight. After adding 1 N hydrochloric acid, methanol was evaporated under reduced pressure. After water was added, the reaction mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. 5 ml of dichloromethane, 68 mg (0.352 mmol) of WSC hydrochloride, 0.039 ml (0.352 mmol) of N-methylpiperazine, 0.049 ml (0.352 mmol) of triethylamine and 3.6 mg (0.029 mmol) of dimethylaminopyridine were added to the residue and the residue was stirred at room temperature overnight. 2 ml of trifluoroacetate was added and stirred at room temperature for 4 hours. After concentration under reduced pressure, saturated aqueous sodium hydrogencarbonate solution was added to basify. After extraction with ethyl acetate, the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by the silica gel chromatography (dichloromethane/methanol=9/1) to obtain the title compound.

Workup

  1. customwas evaporated under reduced pressure
  2. additionAfter water was added
  3. extractionthe reaction mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. stirringthe residue was stirred at room temperature overnight
  7. stirringstirred at room temperature for 4 hours
  8. concentrationAfter concentration under reduced pressure, saturated aqueous sodium hydrogencarbonate solution
  9. additionwas added
  10. extractionAfter extraction with ethyl acetate
  11. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  12. concentrationconcentrated under reduced pressure
  13. customThe residue was purified by the silica gel chromatography (dichloromethane/methanol=9/1)

Sources & evidence

ORD record
ord-3f962656405b456eb6da7dec318d7c52
Source dataset
uspto-grants-2009_02
Patent number
US07494989B2

Reaction notes

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