Sodium Bicarbonate → HCID 10190815, compound

HRID 481005Notes

Reaction equation

HRID 481005 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH:9]1[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([CH2:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[CH2:27][O:28][CH2:29][CH2:30][CH2:31][NH:32]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[NH:12][C:11]([CH2:52][C:53]([N:55]2[CH2:60][CH2:59][N:58]([CH:61]3[CH2:67][CH:66]4[N:68]([CH3:69])[CH:63]([CH2:64][CH2:65]4)[CH2:62]3)[CH2:57][CH2:56]2)=[O:54])=[C:10]1[C:70]([O:72][CH3:73])=[O:71].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>CO.O>[NH2:32][CH2:31][CH2:30][CH2:29][O:28][CH2:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[CH2:20][CH2:19][C:13]1[NH:12][C:11]([CH2:52][C:53]([N:55]2[CH2:60][CH2:59][N:58]([CH:61]3[CH2:62][CH:63]4[N:68]([CH3:69])[CH:66]([CH2:65][CH2:64]4)[CH2:67]3)[CH2:57][CH2:56]2)=[O:54])=[C:10]([C:70]([O:72][CH3:73])=[O:71])[CH:9]([C:3]2[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=2[Cl:8])[C:14]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 18765899HCID 18765899, compound

Product 1

HCID 10190815HCID 10190815, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A mixture of dimethyl 4-(2,6-dichlorophenyl)-2-{2-[4-(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)-1-piperazinyl]-2-oxoethyl}-6-[2-(2-{[3-(tritylamino)propoxy]methyl}phenyl)ethyl]-1,4-dihydro-3,5-pyridinedicarboxylate (355 mg/0.346 mmol) and p-toluenesulfonic acid monohydrate (246 mg/1.29 mmol) in methanol (9.4 ml) and water (3.5 ml) was stirred at reflux temperature for 4 hours. After cooling, the mixture was poured into saturated NaHCO3 aqueous solution. The whole was extracted with dichloromethane (100 ml×2). The combined organic layer was washed with brine (30 ml), dried over magnesium sulfate, filtered and concentrated. The residue was purified by column chromatography (NH2 gel/200-350 mesh/dichloromethane:methanol=100:1-1100:2-100:5) to afford a yellow amorphous (190 mg/70%).

Workup

  1. temperatureat reflux temperature for 4 hours
  2. temperatureAfter cooling
  3. extractionThe whole was extracted with dichloromethane (100 ml×2)
  4. washThe combined organic layer was washed with brine (30 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (NH2 gel/200-350 mesh/dichloromethane:methanol=100:1-1100:2-100:5)
  9. customto afford a yellow amorphous (190 mg/70%)

Sources & evidence

ORD record
ord-85a31dd9f82347f0b95706a56c409079
Source dataset
uspto-grants-2003_11
Patent number
US06653313B2

Reaction notes

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