Triethylamine → HCID 86589738, compound

HRID 2183688Notes

Reaction equation

HRID 2183688 reaction equation
Cl.Cl.[NH2:3][C@H:4]1[C:8]2([CH2:10][CH2:9]2)[CH2:7][NH:6][CH2:5]1.C(N(CC)CC)C.[F:18][B:19][F:20].[F:21][C:22]1[CH:23]=[C:24]2[C:29](=[C:30]([O:33][CH3:34])[C:31]=1F)[N:28]([C@@H:35]1[CH2:37][C@@H:36]1[F:38])[CH:27]=[C:26]([C:39]([OH:41])=[O:40])[C:25]2=[O:42]>CS(C)=O>[NH2:3][C@H:4]1[C:8]2([CH2:10][CH2:9]2)[CH2:7][N:6]([C:31]2[C:30]([O:33][CH3:34])=[C:29]3[C:24]([C:25](=[O:42])[C:26]([C:39]([OH:41])=[O:40])=[CH:27][N:28]3[C@@H:35]3[CH2:37][C@@H:36]3[F:38])=[CH:23][C:22]=2[F:21])[CH2:5]1.[F:18][B:19][F:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 23539486(7S)-5-Azaspiro[2.4]heptan-7-amine--hydrogen chloride (1/2)HCID 86589737HCID 86589737, compound

Product 1

HCID 86589738HCID 86589738, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

(7S)-7-Amino-5-azaspiro[2.4]heptane dihydrochloride (615 mg; 3.32 mmol) and triethylamine (1.40 ml) in dimethylsulfoxide (5 ml) was stirred for 20 minutes at room temperature. 6,7-Difluoro-1-[(1R, 2S)-2-fluoro-1-cyclopropyl]-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid difluoroboron chelate (1.00 g; 2.77 mmol) was added thereto, and the resultant mixture was stirred for 20 hours at room temperature. The reaction mixture was concentrated under reduced pressure, and purified water (50 ml) was added thereto. The pH of the resultant mixture was adjusted to 7.0 with aqueous 1N NaOH solution, and the aqueous layer of the mixture was taken up with chloroform (100 ml×5). The organic layer was dried over sodium sulfate, and the solvent was evaporated. The residue was purified through recrystallization from ethanol, to thereby yield 1.14 g of the title compound as pale yellow crystals (yield: 91%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. custompurified water (50 ml)
  3. additionwas added
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. customthe solvent was evaporated
  6. customThe residue was purified through recrystallization from ethanol

Sources & evidence

ORD record
ord-ff2fbb58fdb54fef87387c976916a619
Source dataset
uspto-grants-2005_05
Patent number
US06900225B2

Reaction notes

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