Triethylamine → Ethyl 8-cyano-1-cyclopropyl-7-[(1S,6S)-2,8-diazabicyclo[4.3.0]nonan-8-yl]-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

HRID 430589Notes

Reaction equation

HRID 430589 reaction equation
[C:1]([C:3]1[C:4](F)=[C:5]([F:22])[CH:6]=[C:7]2[C:12]=1[N:11]([CH:13]1[CH2:15][CH2:14]1)[CH:10]=[C:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8]2=[O:21])#[N:2].[C@@H:24]12[CH2:32][NH:31][CH2:30][C@@H:29]1[CH2:28][CH2:27][CH2:26][NH:25]2.C(N(CC)CC)C>C(#N)C>[C:1]([C:3]1[C:4]([N:31]2[CH2:32][C@@H:24]3[C@@H:29]([CH2:28][CH2:27][CH2:26][NH:25]3)[CH2:30]2)=[C:5]([F:22])[CH:6]=[C:7]2[C:12]=1[N:11]([CH:13]1[CH2:15][CH2:14]1)[CH:10]=[C:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8]2=[O:21])#[N:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10313138(1S,6S)-2,8-Diazabicyclo(4.3.0)nonaneHCID 18417531Ethyl 8-cyano-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Product 1

HCID 15347200Ethyl 8-cyano-1-cyclopropyl-7-[(1S,6S)-2,8-diazabicyclo[4.3.0]nonan-8-yl]-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylateYield 81.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

14.32 g (45 mmol) of ethyl 8-cyano-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate, 6.31 g (50 mmol) of (1S,6S)-2,8-diazabicyclo[4.3.0]nonane and 10.22 g (101 mmol) of triethylamine are boiled under reflux in 270 ml of acetonitrile for 4 hours. The reaction mixture is left to stand at room temperature for some hours and the solid which has crystallized out is filtered off with suction, rinsed with acetonitrile and dried. 15.6 g of a beige solid are obtained (82% of theory).

Workup

  1. waitThe reaction mixture is left
  2. waitto stand at room temperature for some hours
  3. customthe solid which has crystallized out
  4. filtrationis filtered off with suction
  5. washrinsed with acetonitrile
  6. customdried

Sources & evidence

ORD record
ord-c1e5258ce5ac4e9f98010f9779a7169c
Source dataset
uspto-grants-2001_11
Patent number
US06323213B1

Reaction notes

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