(1S,6S)-2,8-Diazabicyclo(4.3.0)nonane → HCID 18665331, compound

HRID 2394304Notes

Reaction equation

HRID 2394304 reaction equation
Cl[C:2]1[C:11]([Cl:12])=[C:10]2[C:5]([C:6](=[O:19])[C:7]([C:16]([OH:18])=[O:17])=[CH:8][N:9]2[CH:13]2[CH2:15][CH2:14]2)=[CH:4][N:3]=1.[C@@H:20]12[CH2:28][NH:27][CH2:26][C@@H:25]1[CH2:24][CH2:23][CH2:22][NH:21]2>CN(C)C=O.C(#N)C>[Cl:12][C:11]1[C:2]([N:27]2[CH2:28][C@@H:20]3[C@@H:25]([CH2:24][CH2:23][CH2:22][NH:21]3)[CH2:26]2)=[N:3][CH:4]=[C:5]2[C:10]=1[N:9]([CH:13]1[CH2:15][CH2:14]1)[CH:8]=[C:7]([C:16]([OH:18])=[O:17])[C:6]2=[O:19]

Participants

5

Reactant 2

HCID 10313138(1S,6S)-2,8-Diazabicyclo(4.3.0)nonaneHCID 189731217,8-Dichloro-1-cyclopropyl-1,4-dihydro-4-oxo-1,6-naphthyridine-3-carboxylic acid

Product 1

HCID 18665331HCID 18665331, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolvent

Procedure

200 mg (0.67 mmol) of 7,8-dichloro-1-cyclopropyl-1,4-dihydro-4-oxo-1,6-naphthyridine-3-carboxylic acid are stirred with 190 mg (1.5 mmol) of (1S,6S)-2,8-diazabicyclo[4.3.0]nonane in a mixture of 1.7 ml of dimethylformamide and 1.7 ml of acetonitrile under argon overnight. The precipitate is isolated and washed with acetonitrile. The crude product is purified on silica gel (eluent: dichloromethane/methanol/aqueous ammonia solution 75:20:25).

Workup

  1. customThe precipitate is isolated
  2. washwashed with acetonitrile
  3. customThe crude product is purified on silica gel (eluent: dichloromethane/methanol/aqueous ammonia solution 75:20:25)

Sources & evidence

ORD record
ord-3937b85528af4856a326fae06cced6c6
Source dataset
uspto-grants-1998_09
Patent number
US05811433

Reaction notes

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