Potassium Carbonate → HCID 59161532, compound

HRID 221976Notes

Reaction equation

HRID 221976 reaction equation
C1(CC([C:10]2[CH:15]=[CH:14][C:13]([C:16]3([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:19][C:18]4([O:23][CH2:22][CH2:21][O:20]4)[CH2:17]3)=[CH:12][CH:11]=2)=O)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[Cl:38][C:39]1[C:44]([CH:45]=O)=[C:43]([NH:47][C:48](=O)OC(C)(C)C)[CH:42]=[CH:41][N:40]=1.C(=O)(O)[O-].[Na+]>CN(C=O)C>[Cl:38][C:39]1[N:40]=[CH:41][CH:42]=[C:43]2[C:44]=1[CH:45]=[C:16]([C:13]1[CH:14]=[CH:15][CH:10]=[CH:11][CH:12]=1)[C:48]([C:10]1[CH:15]=[CH:14][C:13]([C:16]3([NH:24][C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[CH2:19][C:18]4([O:20][CH2:21][CH2:22][O:23]4)[CH2:17]3)=[CH:12][CH:11]=1)=[N:47]2

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 52987944tert-Butyl (2-chloro-3-formylpyridin-4-yl)carbamateHCID 59161539HCID 59161539, compound

Product 1

HCID 59161532HCID 59161532, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of tert-butyl {2-[4-(phenylacetyl)phenyl]-5,8-dioxaspiro[3.4]oct-2-yl}carbamate (1-7) (8.8 g, 20.8 mmol) in DMF (100 mL) was added potassium carbonate (14.4 g, 104 mmol) and tert-butyl (2-chloro-3-formyl-4-pyridinyl)carbamate (1-8) (5.33 g, 20.8 mmol) and the reaction mixture was heated 80° C. over night. The reaction mixture was poured into saturated sodium bicarbonate, extracted with EtOAc, dried over sodium sulfate, filtered and concentrated. The crude residue was purified by column chromatography eluting with 1-80% EtOAc/Hexane. The appropriate fractions were combined and the solvent removed in vacuo to give tert-butyl {2-[4-(5-chloro-3-phenyl-1,6-naphthyridin-2-yl)phenyl]-5,8-dioxaspiro[3.4]oct-2-yl}carbamate (1-9). MS (M+H)+: 545.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by column chromatography
  6. washeluting with 1-80% EtOAc/Hexane
  7. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-d6e671ed5feb4a2fa45bd4642b1c2797
Source dataset
uspto-grants-2012_06
Patent number
US08207169B2

Reaction notes

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