2,6-Difluorobenzoic acid → HCID 13983467, compound

HRID 580459Notes

Reaction equation

HRID 580459 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:3]=1[C:4]([OH:6])=O.[NH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[N:16][C:17]([O:23][CH2:24][CH2:25][CH2:26][N:27]([CH3:29])[CH3:28])=[CH:18][CH:19]=2)[N:14]=1>O>[CH3:29][N:27]([CH3:28])[CH2:26][CH2:25][CH2:24][O:23][C:17]1[N:16]=[C:15]2[C:20]([CH:21]=[CH:22][C:13]([NH:12][C:4](=[O:6])[C:3]3[C:7]([F:11])=[CH:8][CH:9]=[CH:10][C:2]=3[F:1])=[N:14]2)=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 97962,6-Difluorobenzoic acidHCID 13983447HCID 13983447, compound

Product 1

HCID 13983467HCID 13983467, compoundYield 38.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

The procedure is similar to that described in Example 1, but starting with 2,6-difluorobenzoic acid (11.3 g), N,N'-carbonyldiimidazole (12.9 g) and 2-amino-7-(3-dimethylaminopropoxy)-1,8-naphthyridine (11.8 g). The product obtained by precipitation in water followed by drying is dissolved in boiling acetone (450 cc). After 3 hours' cooling at 4° C., the crystallized solid is separated by filtration, washed with acetone (10 cc) and dried at 40° C. under reduced pressure (0.07 kPa). N-[7-(3-Dimethylaminopropoxy)-1,8-naphthyridin-2-yl]-2,6-difluorobenzamide (7.2 g), m.p. 190° C., is obtained.

Workup

  1. customby drying
  2. dissolutionis dissolved
  3. customthe crystallized solid is separated by filtration
  4. washwashed with acetone (10 cc)
  5. customdried at 40° C. under reduced pressure (0.07 kPa)

Sources & evidence

ORD record
ord-6bfc75c2ea5049c19a712faf42e1b5d5
Source dataset
uspto-grants-1988_06
Patent number
US04753933

Reaction notes

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