1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → N-[5-(3,5-Difluoro-benzyl)-1H-indazol-3-yl]-4-(4-methyl-piperazine-1-carbonyl)-2-nitro-benzamide

HRID 512961노트

반응식

HRID 512961 반응식
[F:1][C:2]1[CH:3]=[C:4]([CH:30]=[C:31]([F:33])[CH:32]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[NH:15][C:16]([C:18]1[CH:26]=[CH:25][C:21]([C:22]([OH:24])=O)=[CH:20][C:19]=1[N+:27]([O-:29])=[O:28])=[O:17].ON1C2C=CC=CC=2N=N1.CCN=C=NCCCN(C)C.[CH3:55][N:56]1[CH2:61][CH2:60][NH:59][CH2:58][CH2:57]1>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:30]=[C:31]([F:33])[CH:32]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[NH:15][C:16](=[O:17])[C:18]1[CH:26]=[CH:25][C:21]([C:22]([N:59]2[CH2:60][CH2:61][N:56]([CH3:55])[CH2:57][CH2:58]2)=[O:24])=[CH:20][C:19]=1[N+:27]([O-:29])=[O:28]

참가 물질

6

반응물 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 686709434-{[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]carbamoyl}-3-nitrobenzoic acid

생성물 1

HCID 68671439N-[5-(3,5-Difluoro-benzyl)-1H-indazol-3-yl]-4-(4-methyl-piperazine-1-carbonyl)-2-nitro-benzamide수율 99.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4-{[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]carbamoyl}-3-nitrobenzoic acid (500 mg, 1.11 mmol) in DMF (10 mL) was treated with 1-hydroxybenzotriazole (195 mg, 1.44 mmol), EDCI (276 mg, 1.44 mmol) and 1-methylpiperazine (0.16 mL, 1.44 mmol). The reaction was left at room temperature over night. The volatiles were removed by evaporation, the residue was added drop-wise to iced-water (25 mL) with stirring. A yellow solid was obtained which was extracted with DCM (2×25 mL). The combined organic layers were dried over sodium sulphate and evaporated leaving 590 mg of title compound which was employed in the following step without any further purification.

후처리

  1. waitThe reaction was left at room temperature over night
  2. customThe volatiles were removed by evaporation
  3. additionthe residue was added drop-wise to iced-water (25 mL)
  4. customA yellow solid was obtained which
  5. extractionwas extracted with DCM (2×25 mL)
  6. dry with materialThe combined organic layers were dried over sodium sulphate
  7. customevaporated

출처 및 근거

ORD 기록
ord-92730fc126974f7ab4f7e441e6e41a6f
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102662B2

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