Potassium Carbonate → HCID 131721344, compound

HRID 1739114Notes

Reaction equation

HRID 1739114 reaction equation
[OH-].[Na+].O.Cl.[Cl:5][C:6]1[CH:7]=[C:8]([CH:13]([CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][C:30](COC(NCC)=O)([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:29][CH2:28]2)[CH2:14][N:15]([CH3:24])[C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:9]=[CH:10][C:11]=1[Cl:12].O.O.[Cl:48]C1C=C(C(CCN2CCC(C3C=CC=CC=3)(COC(NCC)=O)CC2)C[N:58](C)[C:59](=[O:66])C2C=CC=CC=2)C=CC=1Cl.Cl.C([O-])([O-])=O.[K+].[K+]>O.C(#N)C.Cl>[OH2:23].[ClH:5].[Cl:5][C:6]1[CH:7]=[C:8]([CH:13]([CH2:25][CH2:26][N:27]2[CH2:28][CH2:29][C:30]([NH:58][CH:59]=[O:66])([C:33]3[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=3)[CH2:31][CH2:32]2)[CH2:14][N:15]([CH3:24])[C:16](=[O:23])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:9]=[CH:10][C:11]=1[Cl:12].[Cl:5][C:6]1[CH:7]=[C:8]([CH:13]([CH2:25][CH2:26][N:27]2[CH2:28][CH2:29][C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)([NH:58][CH:59]=[O:66])[CH2:31][CH2:32]2)[CH2:14][N:15]([CH3:24])[C:16](=[O:23])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:9]=[CH:10][C:11]=1[Cl:12].[ClH:48]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 131721345HCID 131721345, compound

Product 1

HCID 131721344HCID 131721344, compoundYield 203.5%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

0.55 g of the compound obtained in PREPARATION 1.3 is dissolved in water, the mixture is alkalinized by adding concentrated NaOH solution, the product is extracted with DCM, the organic phase is dried over MgSO4 and the solvent is evaporated off under vacuum. The product obtained is taken up in 20 ml of acetonitrile, 0.85 g of the compound obtained in step C of EXAMPLE 15 and 1 g of K2CO3 are added and the reaction mixture is heated to reflux for 2 hours 30 minutes. It is concentrated under vacuum, the residue is extracted with AcOEt, the organic phase is washed with water and with 5% NaOH solution and dried over MgSO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica H, eluting with DCM and then with a DCM/MeOH (90:10; v/v) mixture. The product obtained is taken up in ethereal hydrogen chloride and the precipitate formed is drained. 0.51 g of the expected product is obtained.

Workup

  1. extractionthe product is extracted with DCM
  2. dry with materialthe organic phase is dried over MgSO4
  3. customthe solvent is evaporated off under vacuum
  4. customThe product obtained
  5. temperaturethe reaction mixture is heated
  6. temperatureto reflux for 2 hours 30 minutes
  7. concentrationIt is concentrated under vacuum
  8. extractionthe residue is extracted with AcOEt
  9. washthe organic phase is washed with water and with 5% NaOH solution
  10. dry with materialdried over MgSO4
  11. customthe solvent is evaporated off under vacuum
  12. customThe residue is chromatographed on silica H
  13. washeluting with DCM
  14. customThe product obtained
  15. customthe precipitate formed

Sources & evidence

ORD record
ord-e84a704cde914378b735e771a15f6411
Source dataset
uspto-grants-1999_10
Patent number
US05965580

Reaction notes

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