Ethanol → N-(7-methoxy-1,8-naphthyridin-2-yl)-2,6-difluorobenzamide

HRID 235815Notes

Reaction equation

HRID 235815 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][CH3:24])=[CH:18][CH:19]=2)[N:14]=1.C(O)C>O>[CH3:24][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

5

Reactant 3

HCID 702EthanolHCID 97962,6-Difluorobenzoic acidHCID 217930277-methoxy-1,8-Naphthyridin-2-amine

Product 1

HCID 20217540N-(7-methoxy-1,8-naphthyridin-2-yl)-2,6-difluorobenzamideYield 40.4%

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 (5.1 g), N,N'-carbonyldiimidazole (5.2 g) and 2-amino-7-methoxy-1,8-naphthyridine (4.4 g). The product produced by precipitation in water (4.5 g; m.p. 215°-217° C.) is dissolved in boiling ethanol (70 cc). After 1 hour's cooling at 4° C., the crystallised solid is separated by filtration, washed with ethanol (10 cc) and dried at 45° C. under reduced pressure (0.067 kPa). N-(7-methoxy-1,8-naphthyridin-2-yl)-2,6-difluorobenzamide (3.2 g) is produced, m.p. 219°-220° C.

Workup

  1. dissolutionis dissolved
  2. customthe crystallised solid is separated by filtration
  3. washwashed with ethanol (10 cc)
  4. customdried at 45° C. under reduced pressure (0.067 kPa)

Sources & evidence

ORD record
ord-48b605eb739444d7ad11458a312f483c
Source dataset
uspto-grants-1987_02
Patent number
US04642308

Reaction notes

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