Diisopropylamine → HCID 53341080, compound

HRID 715714Notes

Reaction equation

HRID 715714 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[CH:16][CH:17]=[N:18]3)=[C:13](OS(C(F)(F)F)(=O)=O)[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[NH2:29][CH2:30][C:31]1[O:35][C:34](=[O:36])[NH:33][N:32]=1.C(NC(C)C)(C)C>CC(N(C)C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[CH:20]=[C:19]3[C:14]([CH:15]=[CH:16][CH:17]=[N:18]3)=[C:13]([NH:29][CH2:30][C:31]3[O:35][C:34](=[O:36])[NH:33][N:32]=3)[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 7912Diisopropylamine2×HCID 24950198HCID 24950198, compoundHCID 58071886HCID 58071886, compound

Product 1

HCID 53341080HCID 53341080, compound

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
70 °C

Procedure

97 mg Trifluoromethanesulfonic acid 7-(3,4-dimethoxy-phenyl)-[1,6]-naphthyridine-5-yl ester (6.2), 30 mg 5-aminomethyl-3H-[1,3,4]oxadiazole-2-one (2.33) and 0.132 mL N,N-diisopropylamine were placed in dimethylacetamide at ambient temperature. The reaction was heated to 70° C. overnight. After this time the reaction was cooled to ambient temperature and additional 0.132 mL N,N-diisopropylamine were added. The reaction was heated to 90° C. for 6 h. After this time, the mixture was cooled to ambient temperature and partitioned between water and ethyl acetate. The organic phase was separated and the aqueous phase was extracted with additional ethyl acetate (×3) and the combined organic fractions were dried over sodium sulfate, filtered and the solvent was concentrated from the filtrate under reduced pressure. Purification by and then by silica gel chromatography (ethyl acetate/methanol: 100:0 to 95:5) provided the title compound.

Workup

  1. temperatureAfter this time the reaction was cooled to ambient temperature
  2. temperatureThe reaction was heated to 90° C. for 6 h
  3. temperatureAfter this time, the mixture was cooled to ambient temperature
  4. custompartitioned between water and ethyl acetate
  5. customThe organic phase was separated
  6. extractionthe aqueous phase was extracted with additional ethyl acetate (×3)
  7. dry with materialthe combined organic fractions were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationthe solvent was concentrated from the filtrate under reduced pressure
  10. customPurification by and then by silica gel chromatography (ethyl acetate/methanol: 100:0 to 95:5)

Sources & evidence

ORD record
ord-adc6104c22bf420088bc9a7bd271fa35
Source dataset
uspto-grants-2015_11
Patent number
US09187478B2

Reaction notes

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