Benzoic Acid → N-[7-(4-chlorophenoxy)-1,8-naphthyridin-2-yl]benzamide

HRID 2413929

반응식

HRID 2413929 반응식
[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]([O:21][C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=3)=[CH:16][CH:17]=2)[N:12]=1>O>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([O:21][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)=[CH:23][CH:24]=1

참가 물질

4

반응물 2

HCID 243Benzoic AcidHCID 137873742-Amino-7-(4-chlorophenoxy)-1,8-naphthyridine

생성물 1

HCID 13787388N-[7-(4-chlorophenoxy)-1,8-naphthyridin-2-yl]benzamide수율 23%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

The procedure is analogous to that described in Example 1, but starting with benzoic acid (12.6 g), N,N'-carbonyldiimidazole (7.45 g) and 2-amino-7-(4-chlorophenoxy)-1,8-naphthyridine (12.6 g). The product obtained by precipitation in water (13 g; m.p. 100° C.) is purified by chromatography on a 4-cm-diameter column containing silica (0.040-0.063 mm; 200 g), eluting with methylene chloride and collecting 100-cc fractions. The fractions 10 to 25 are concentrated to 9/10 of the initial volume. After cooling for 2 hours at 0° C., the crystallized solid is separated by filtration, washed with diethyl ether (2×5 cc) and dried at 40° C. under reduced pressure (0.07 kPa). N-[7-(4-chlorophenoxy)-1,8-naphthyridin-2-yl]benzamide (4 g), m.p. 148° C., is obtained.

후처리

  1. customis purified by chromatography on a 4-cm-diameter column
  2. additioncontaining silica (0.040-0.063 mm; 200 g)
  3. washeluting with methylene chloride
  4. customcollecting 100-cc fractions
  5. concentrationThe fractions 10 to 25 are concentrated to 9/10 of the initial volume
  6. customthe crystallized solid is separated by filtration
  7. washwashed with diethyl ether (2×5 cc)
  8. customdried at 40° C. under reduced pressure (0.07 kPa)

출처 및 근거

ORD 기록
ord-803155e27bea47b19d4a9decaf42cc28
출처 데이터셋
uspto-grants-1988_01
특허 번호
US04720500

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