Potassium Carbonate → HCID 58524878, compound

HRID 1678799Notes

Reaction equation

HRID 1678799 reaction equation
[C:1]1([CH2:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]3([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:18][CH2:17]3)=[CH:12][CH:11]=2)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:27][C:28]1[C:33]([CH:34]=O)=[C:32]([NH:36]C(=O)OC(C)(C)C)[CH:31]=[CH:30][N:29]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[Cl:27][C:28]1[N:29]=[CH:30][CH:31]=[C:32]2[C:33]=1[CH:34]=[C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:8]([C:10]1[CH:11]=[CH:12][C:13]([C:16]3([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[CH2:17][CH2:18]3)=[CH:14][CH:15]=1)=[N:36]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 52987944tert-Butyl (2-chloro-3-formylpyridin-4-yl)carbamateHCID 59473065HCID 59473065, compound

Product 1

HCID 58524878HCID 58524878, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 33-2 (0.64 g, 2.5 mmol), 3-1 (0.88 g, 2.5 mmol) and potassium carbonate (2.1 g, 15 mmol) in DMF (14 mL) was heated to 120° C. for 4.5 hours. The reaction was cooled to room temperature, diluted with ethyl acetate, washed with water, brine, dried over sodium sulfate, filtered and concentrated. Purification by silica gel chromatography (1% ethyl acetate/hexane→70% ethyl acetate/hexane) gave the title compound as a foam. MS (M+H+): calculated=471.98, observed=472.1.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (1% ethyl acetate/hexane→70% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6c4b66f8b7944b56b27893ec6a6b6aa3
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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