Dimethylformamide → HCID 13787385, compound

HRID 2413923Notes

Reaction equation

HRID 2413923 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=O)=[CH:5][CH:4]=1.[NH2:13][C:14]1[CH:23]=[CH:22][C:21]2[C:16](=[N:17][C:18]([Cl:24])=[CH:19][CH:20]=2)[N:15]=1.CN(C)C=O>O>[Cl:24][C:18]1[N:17]=[C:16]2[C:21]([CH:22]=[CH:23][C:14]([NH:13][C:7](=[O:9])[C:6]3[CH:5]=[CH:4][C:3]([N:2]([CH3:1])[CH3:12])=[CH:11][CH:10]=3)=[N:15]2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 120924-(Dimethylamino)benzoic acidHCID 851997-Chloro-1,8-naphthyridin-2-amine

Product 1

HCID 13787385HCID 13787385, compoundYield 31.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

The procedure is analogous to that described in Example 1, but starting with 4-dimethylaminobenzoic acid (14.9 g), N,N'-carbonyldiimidazole (14.6 g) and 2-amino-7-chloro-1,8-naphthyridine (10.8 g). The crude product obtained by filtration of the reaction mixture (6.4 g; m.p. 248° C.) is dissolved in boiling dimethylformamide (95 cc). After cooling for 2 hours at 20° C., water (95 cc) is added. The crystallized solid is separated by filtration, washed with a dimethylformamide/water (50:50 by volume) mixture (2×10 cc), and dried at 45° C. under reduced pressure (0.07 kPa). N-(7-Chloro-1,8-naphthyridin-2-yl)-4-dimethylaminobenzamide (6.2 g), m.p. 248° C., is obtained.

Workup

  1. customThe crude product obtained by filtration of the reaction mixture (6.4 g; m.p. 248° C.)
  2. dissolutionis dissolved
  3. customThe crystallized solid is separated by filtration
  4. washwashed with a dimethylformamide/water (50:50 by volume) mixture (2×10 cc)
  5. customdried at 45° C. under reduced pressure (0.07 kPa)

Sources & evidence

ORD record
ord-05e41dc766aa4c1ebf92a60036bb1c4a
Source dataset
uspto-grants-1988_01
Patent number
US04720500

Reaction notes

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