1-Propanol → HCID 20154390, compound

HRID 2413938Notes

Reaction equation

HRID 2413938 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[NH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[N:15][C:16]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)=[CH:17][CH:18]=2)[N:13]=1.C(O)CC>O>[F:28][C:25]1[CH:24]=[CH:23][C:22]([C:16]2[N:15]=[C:14]3[C:19]([CH:20]=[CH:21][C:12]([NH:11][C:5](=[O:7])[C:4]4[CH:8]=[CH:9][CH:10]=[C:2]([Br:1])[CH:3]=4)=[N:13]3)=[CH:18][CH:17]=2)=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 10311-PropanolHCID 114563-Bromobenzoic acidHCID 13983420HCID 13983420, compound

Product 1

HCID 20154390HCID 20154390, compoundYield 46.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

The procedure is analogous to that described in Example 11, but starting with 3-bromobenzoic acid (2.1 g), N,N'-carbonyldiimidazole (1.6 g) and 2-amino-7-(4-fluorophenyl)-1,8-naphthyridine (1.7 g). The product obtained by precipitation in water (2 g) is dissolved in boiling propanol (200 cc). After cooling for 4 hours at 4° C., the crystallized solid is separated by filtration, washed with propanol (3×10 cc) and dried at 40° C. under reduced pressure (0.07 kPa). N-[7-(4-Fluorophenyl)-1,8-naphthyridin-2-yl]-3-bromobenzamide (1.4 g), m.p. 210° C., is obtained.

Workup

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

Sources & evidence

ORD record
ord-473feb0796e1420294c4732a6888c72e
Source dataset
uspto-grants-1988_01
Patent number
US04720500

Reaction notes

Loading…