2-Furancarbonyl chloride → HCID 69480848, compound

HRID 2364393Notes

Reaction equation

HRID 2364393 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([CH2:15][C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[CH:13]=2)[C:8]([OH:23])=[C:7]([C:24]([NH:26][CH2:27][CH2:28][O:29][CH2:30][CH3:31])=[O:25])[C:6]1=[O:32].[O:33]1[CH:37]=[CH:36][CH:35]=[C:34]1[C:38](Cl)=[O:39].CCN(C(C)C)C(C)C>CN(C=O)C>[CH2:30]([O:29][CH2:28][CH2:27][NH:26][C:24]([C:7]1[C:6](=[O:32])[N:5]([CH2:4][CH2:3][CH2:2][NH:1][C:38]([C:34]2[O:33][CH:37]=[CH:36][CH:35]=2)=[O:39])[C:14]2[C:9]([C:8]=1[OH:23])=[N:10][CH:11]=[C:12]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=1)[CH:13]=2)=[O:25])[CH3:31]

Participants

5

Reactant 3

HCID 682422-Furancarbonyl chlorideHCID 81531DiisopropylethylamineHCID 69481020HCID 69481020, compound

Product 1

HCID 69480848HCID 69480848, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1-(3-aminopropyl)-N-[2-(ethyloxy)ethyl]-7-[(4-fluorophenyl)methyl]-4-hydroxy-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxamide (25 mg, 0.057), 2-furancarbonyl chloride (5.8 μL, 0.059 mmol) and DIEA (49 μL, 0.282 mmol) was combined in anhydrous DMF (1.5 mL). After stirring under nitrogen at ambient temperature for 0.5 hrs, the reaction mixture was evaporated in vacuo and partitioned between EtOAc and 1N NaHSO4. The aqueous layer was separated and back-extracted with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered, and evaporated in vacuo. The product was crystallized from MeOH/Et2O and collected by filtration providing a white solid: ES+ MS: 537 (M+H+).

Workup

  1. customthe reaction mixture was evaporated in vacuo
  2. custompartitioned between EtOAc and 1N NaHSO4
  3. customThe aqueous layer was separated
  4. extractionback-extracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe product was crystallized from MeOH/Et2O
  10. filtrationcollected by filtration
  11. customproviding a white solid

Sources & evidence

ORD record
ord-a329def9f86d4682a97a724efc337958
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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