Cyclohexanecarboxylic acid → 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-(4-cyclohexylcarbonylpiperazin-1-yl)carbonyloxy-isoindolin-1-one

HRID 27079

반응식

HRID 27079 반응식
[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[CH:20]([O:21][C:22]([N:24]4[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]4)=[O:23])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:30])=[N:9]2)=[CH:4][CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1.[CH:46]1([C:52](O)=[O:53])[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1>C(Cl)Cl>[Cl:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([N:12]3[CH:20]([O:21][C:22]([N:24]4[CH2:25][CH2:26][N:27]([C:52]([CH:46]5[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]5)=[O:53])[CH2:28][CH2:29]4)=[O:23])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:30])=[N:9]2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 7413Cyclohexanecarboxylic acidHCID 10868DicyclohexylcarbodiimideHCID 233436392-(7-Chloro-1,8-naphthyridin-2-yl)-3-(piperazin-1-yl)carbonyloxy-isoindolin-1-one

생성물 1

HCID 137286392-(7-Chloro-1,8-naphthyridin-2-yl)-3-(4-cyclohexylcarbonylpiperazin-1-yl)carbonyloxy-isoindolin-1-one수율 69.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

The procedure of Example 14 is followed but starting with 2-(7-chloro-1,8-naphthyridin-2-yl)-3-(piperazin-1-yl)carbonyloxy-isoindolin-1-one (4.23 g.), N,N'-dicyclohexylcarbodiimide (3.1 g.) in anhydrous methylene chloride (100 cc.) and cyclohexylcarboxylic acid (1.92 g.). After having filtered off the precipitate, the organic solution is washed with an 8% aqueous solution of sodium bicarbonate (20 cc.) and then dried over anhydrous potassium carbonate (10 g.). After the solution has been filtered and the filtrate concentrated to dryness, the residue is recrystallised from ethanol (300 cc.). 2-(7-Chloro-1,8-naphthyridin-2-yl)-3-(4-cyclohexylcarbonylpiperazin-1-yl)carbonyloxy-isoindolin-1-one (3.7 g.), which melts at 240° C., is thus obtained.

후처리

  1. filtrationAfter having filtered off the precipitate
  2. washthe organic solution is washed with an 8% aqueous solution of sodium bicarbonate (20 cc.)
  3. dry with materialdried over anhydrous potassium carbonate (10 g.)
  4. filtrationAfter the solution has been filtered
  5. concentrationthe filtrate concentrated to dryness
  6. customthe residue is recrystallised from ethanol (300 cc.)

출처 및 근거

ORD 기록
ord-33753e00e901425a81626c524cf476cf
출처 데이터셋
uspto-grants-1980_09
특허 번호
US04220646

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