N~1~-(Pyridin-2-yl)ethane-1,2-diamine → HCID 24753198, compound

HRID 561095Notes

Reaction equation

HRID 561095 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:17][CH2:16]1.[N:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH:28][CH2:29][CH2:30][NH2:31]>CS(C)=O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([NH:31][CH2:30][CH2:29][NH:28][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][N:22]=2)[C:9]([F:14])=[C:8]2[C:3]=1[C:4](=[O:21])[C:5]([C:18]([OH:20])=[O:19])=[CH:6][N:7]2[CH:15]1[CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 410428N~1~-(Pyridin-2-yl)ethane-1,2-diamineHCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 24753198HCID 24753198, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 7 (270 mg, 0.91 mmol) and N-2-pyridinyl-1,2-ethanediamine (250 mg, 1.82 mmol) in DMSO (7 mL) was stirred at 80° C. for 1 h. The reaction mixture was cooled and freeze-dried overnight. The crude product was taken up in methanol (75 mL) and the resulting precipitate was removed by filtration, washed with cold methanol and dried to yield 8 (285 mg, 75%) as a yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customfreeze-dried overnight
  3. customthe resulting precipitate was removed by filtration
  4. washwashed with cold methanol
  5. customdried

Sources & evidence

ORD record
ord-77043daa71204de6876e693554c27133
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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