Nitrogen → HCID 19865441, compound

HRID 414736Notes

Reaction equation

HRID 414736 reaction equation
[OH-].[OH:2][C:3]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[N:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5](=[O:19])[C:4]=1[NH+:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1.[CH2:25]([N:27]([CH2:31][CH3:32])[C:28](Cl)=[O:29])[CH3:26].N#N.N12CCCN=C1CCCCC2>N1C=CC=CC=1.C(O)(=O)C.CN(C)C=O.C(N(CC)CC)C>[CH2:25]([N:27]([CH2:31][CH3:32])[C:28]([O:2][C:3]1[C:12]2[C:7](=[N:8][CH:9]=[CH:10][CH:11]=2)[N:6]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5](=[O:19])[C:4]=1[N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:29])[CH3:26]

Participants

9

Reactant 4

HCID 947NitrogenHCID 6916Diethylcarbamoyl chloride2×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 54680203HCID 54680203, compound

Product 1

HCID 19865441HCID 19865441, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1-(1,2-dihydro-4-hydroxy-1-phenyl-2-oxo-1,8-naphthyridin-3-yl)-pyrrolidinium hydroxide, inner salt (3 g), triethylamine (1.88 g), and diethylcarbamoyl chloride (1.57 g) in dry pyridine (50 mL) was stirred overnight at room temperature in an N2 atmosphere. Some starting material remained so dimethylformamide (50 mL), 1,8-diazabicyclo[5.4.0]undec7-ene (DBU) (2.83 g), and diethylcarbamoyl chloride (1.57 g) were added and the mixture was heated at 80° C. for 0.5 hour. The reaction mixture was then poured over ice and the pH was adjusted to about 6 with acetic acid. The resulting solution was extracted three times with ethyl acetate. The organic extracts were combined, dried (Na2SO4), filtered and evaporated to a solid which was recrystallized from isopropanol to yield the desired product, 2.03 g (54%), m.p. 158°-160° C.

Workup

  1. additionwere added
  2. additionThe reaction mixture was then poured over ice
  3. extractionThe resulting solution was extracted three times with ethyl acetate
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated to a solid which
  7. customwas recrystallized from isopropanol

Sources & evidence

ORD record
ord-90bdb6d1793844498e0de311b6f82ca0
Source dataset
uspto-grants-1988_12
Patent number
US04794116

Reaction notes

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