1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 54380980, compound

HRID 1742936Notes

Reaction equation

HRID 1742936 reaction equation
Cl[C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:20])[C:7]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:8][N:9]2[CH:12]2[CH2:14][CH2:13]2)=[CH:4][C:3]=1[F:21].Cl.[N:23]1([C@H:28]2[CH2:32][CH2:31][NH:30][CH2:29]2)[CH:27]=[CH:26][N:25]=[N:24]1.C1CCN2C(=NCCC2)CC1>N1C=CC=CC=1>[CH:12]1([N:9]2[C:10]3[C:5](=[CH:4][C:3]([F:21])=[C:2]([N:30]4[CH2:31][CH2:32][C@H:28]([N:23]5[CH:27]=[CH:26][N:25]=[N:24]5)[CH2:29]4)[N:11]=3)[C:6](=[O:20])[C:7]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:8]2)[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 11722954Ethyl 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylateHCID 70283282HCID 70283282, compound

Product 1

HCID 54380980HCID 54380980, compoundYield 24.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Ethyl 7-chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (250 mg, 0.8 mmol) was reacted with 350 mg (2 mmol) of 3(S)-(1,2,3-triazol-1-yl)pyrrolidine hydrochloride in 8 ml of pyridine in the presence of 305 mg (2 mmol) of DBU at 80°-90° C. for 6 h. The reaction was then stirred at r.t. for 4 days. The solvent was then evaporated under reduced pressure and to the residue, water was added and extracted with chloroform. The organic layer was dried and evaporated to dryness. The residue was then chromatographed over alumina (neutral, activity III) using chloroform as solvent to yield 80 mg (24%) of the desired product. 1H NMR (CDCl3) δ: 8.48 (s, 1H), 8.05 (d, 1H), 7.76 (d, 1H), 7.71 (d, 1H), 5.46-5.32 (m, 1H), 4.46-4.26 (m, 4H), 4.15-4.0 (m, 2H), 3.56-3.42 (m, 1H), 2.71-2.57 (m, 2H), 1.4 (t, 3H), 1.26-0.95 (m, 4H).

Workup

  1. customThe solvent was then evaporated under reduced pressure and to the residue, water
  2. additionwas added
  3. extractionextracted with chloroform
  4. customThe organic layer was dried
  5. customevaporated to dryness
  6. customThe residue was then chromatographed over alumina (neutral, activity III)

Sources & evidence

ORD record
ord-9500cac570f54815a702a1145013067c
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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