Hydrochloric Acid → HCID 10234412, compound

HRID 481012Notes

Reaction equation

HRID 481012 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22][CH2:23][C:24]2[NH:25][C:26]([CH2:46][C:47]([N:49]3[CH2:54][CH2:53][N:52]([CH:55]4[CH2:61][CH:60]5[N:62]([CH3:63])[CH:57]([CH2:58][CH2:59]5)[CH2:56]4)[CH2:51][CH2:50]3)=[O:48])=[C:27]([C:42]([O:44][CH3:45])=[O:43])[CH:28]([C:34]3[C:39]([Cl:40])=[CH:38][CH:37]=[CH:36][C:35]=3[Cl:41])[C:29]=2[C:30]([O:32][CH3:33])=[O:31])=[O:15])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.C([O-])(O)=O.[Na+]>>[Cl:40][C:39]1[CH:38]=[CH:37][CH:36]=[C:35]([Cl:41])[C:34]=1[CH:28]1[C:29]([C:30]([O:32][CH3:33])=[O:31])=[C:24]([CH2:23][CH2:22][C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[C:14]([N:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)=[O:15])[NH:25][C:26]([CH2:46][C:47]([N:49]2[CH2:54][CH2:53][N:52]([CH:55]3[CH2:56][CH:57]4[N:62]([CH3:63])[CH:60]([CH2:59][CH2:58]4)[CH2:61]3)[CH2:51][CH2:50]2)=[O:48])=[C:27]1[C:42]([O:44][CH3:45])=[O:43]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 18765905HCID 18765905, compound

Product 1

HCID 10234412HCID 10234412, compound

Procedure

A mixture of dimethyl 2-[2-(2-{[4-(tert-butoxycarbonyl)-1-piperazinyl]carbonyl}phenyl)ethyl]-4-(2,6-dichlorophenyl)-6-{2-[4-(8-methyl-8-azabicyclo[3.2.1]oct-3-yl)-1-piperazinyl]-2-oxoethyl}-1,4-dihydro-3,5-pyridinedicarboxylate (368 mg/0.41 mmol) and 2N HCl aqueous solution (8 ml/16 mmol) was refluxed for 2 hours. After cooling down, the mixture was basitified with saturated NaHCO3 aqueous solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by column chromatography on NH2 gel (CH2Cl2:MeOH=200:1-20:1) to afford 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-(1-piperazinylcarbonyl)phenyl]ethyl}-1,4-dihydro-3,5-pyridinedicarboxylate as a yellow amorphous.

Workup

  1. temperaturewas refluxed for 2 hours
  2. temperatureAfter cooling down
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on NH2 gel (CH2Cl2:MeOH=200:1-20:1)

Sources & evidence

ORD record
ord-d5f9bee419434353ab87a6c3ddeb5dbf
Source dataset
uspto-grants-2003_11
Patent number
US06653313B2

Reaction notes

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