Acetonitrile → HCID 13787383, compound

HRID 2413919Notes

Reaction equation

HRID 2413919 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]([Cl:25])=[CH:20][CH:21]=2)[N:16]=1.C(#N)C>O>[Cl:25][C:19]1[N:18]=[C:17]2[C:22]([CH:23]=[CH:24][C:15]([NH:14][C:7](=[O:9])[C:6]3[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:13])[F:12])=[CH:11][CH:10]=3)=[N:16]2)=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 99664-(Trifluoromethyl)benzoic acidHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 13787383HCID 13787383, compoundYield 77.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
4 °C

Procedure

The procedure is analogous to that described in Example 1, but starting with 4-trifluoromethylbenzoic acid (10 g), N,N'-carbonyldiimidazole (8.4 g) and 2-amino-7-chloro-1,8-naphthyridine (5.9 g). The product obtained by precipitation in water (11.5 g; m.p. 236° C.) is dissolved in boiling acetonitrile (250 cc). After cooling for 4 hours at 4° C., the crystallized solid is separated by filtration, washed with acetonitrile (2×20 cc) and dried at 45° C. under reduced pressure (0.07 kPa). N-(7-Chloro-1,8-naphthyridin-2-yl)-4-trifluoromethylbenzamide (9 g), m.p. 236° C., is obtained.

Workup

  1. dissolutionis dissolved
  2. customthe crystallized solid is separated by filtration
  3. washwashed with acetonitrile (2×20 cc)
  4. customdried at 45° C. under reduced pressure (0.07 kPa)

Sources & evidence

ORD record
ord-69f0cfa51d2241ebb2420c7717cd158a
Source dataset
uspto-grants-1988_01
Patent number
US04720500

Reaction notes

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