Acetonitrile → HCID 20154395, compound

HRID 2413922Notes

Reaction equation

HRID 2413922 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.[NH2:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[N:18][C:19]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)=[CH:20][CH:21]=2)[N:16]=1.C(#N)C>O>[CH3:32][O:31][C:28]1[CH:27]=[CH:26][C:25]([C:19]2[N:18]=[C:17]3[C:22]([CH:23]=[CH:24][C:15]([NH:14][C:7](=[O:9])[C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:13])[F:12])=[CH:11][CH:10]=4)=[N:16]3)=[CH:21][CH:20]=2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 99664-(Trifluoromethyl)benzoic acidHCID 13983419HCID 13983419, compound

Product 1

HCID 20154395HCID 20154395, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

The procedure is analogous to that described in Example 1 below but starting with 4-trifluoromethylbenzoic acid (2.7 g), N,N'-carbonyldiimidazole (2.3 g) and 2-amino-7-(4-methoxyphenyl)-1,8-naphthyridine (2.5 g). The product obtained by precipitation in water (3.3 g; m.p. 144°-146° C.) is dissolved in boiling acetonitrile (100 cc). After cooling for 3 hours at 4° C., the crystallized solid is separated by filtration, washed with acetonitrile (2×10 cc) and dried at 40° C. under reduced pressure (0.07 kPa). N-[7-(4-Methoxyphenyl)-1,8-naphthyridin-2-yl]-4-trifluoromethylbenzamide (2.4 g), m.p. 148° C., is obtained.

Workup

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

Sources & evidence

ORD record
ord-c927d3a79faf48039906ad4e84322ba9
Source dataset
uspto-grants-1988_01
Patent number
US04720500

Reaction notes

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