Benzoic Acid → HCID 13787389, compound

HRID 2413931Notes

Reaction equation

HRID 2413931 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[N:14][C:15]([N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:16][CH:17]=2)[N:12]=1.C(#N)C>O>[N:21]1([C:15]2[N:14]=[C:13]3[C:18]([CH:19]=[CH:20][C:11]([NH:10][C:1](=[O:9])[C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[N:12]3)=[CH:17][CH:16]=2)[CH2:22][CH2:23][CH2:24][CH2:25]1

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 6342AcetonitrileHCID 13787375HCID 13787375, compound

Product 1

HCID 13787389HCID 13787389, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

The procedure is analogous to that described in Example 1, but starting with benzoic acid (6.5 g), N,N'-carbonyldiimidazole (8.6 g) and 2-amino-7-(1-pyrrolidinyl)-1,8-naphthyridine (8.6 g). The product obtained by precipitation in water (13 g; m.p. 110° C.) is dissolved in boiling acetonitrile (85 cc). After cooling for 2 hours at 4° C., the crystallized solid is separated by filtration, washed with acetonitrile (15 cc) and dried at 40° C. under reduced pressure (0.07 kPa). N-[7-(1-Pyrrolidinyl)-1,8-naphthyridin-2-yl]benzamide (11.5 g), m.p. 130° C., is obtained.

Workup

  1. dissolutionis dissolved
  2. customthe crystallized solid is separated by filtration
  3. washwashed with acetonitrile (15 cc)
  4. customdried at 40° C. under reduced pressure (0.07 kPa)

Sources & evidence

ORD record
ord-137b089ceff1432682ee4ea403ab3dd8
Source dataset
uspto-grants-1988_01
Patent number
US04720500

Reaction notes

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