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1-Hydroxybenzotriazole → 5-(2-Cyano-phenoxy)-2-pyridazin-3-yl-6-(4-methanesulfonyl-phenoxy)-1H-benzimidazole

HRID 13240
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HRID 13240 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7](O)=O)[N:2]=1.ON1C2C=CC=CC=2N=N1.[H-].CN(C)CCCN=C=NCC.[C:32]([C:34]1[CH:66]=[CH:65][CH:64]=[CH:63][C:35]=1[O:36][C:37]1[C:51]([O:52][C:53]2[CH:58]=[CH:57][C:56]([S:59]([CH3:62])(=[O:61])=[O:60])=[CH:55][CH:54]=2)=[CH:50][C:40]2[NH:41]C(C3C=CC=CN=3)=[N:43][C:39]=2[CH:38]=1)#[N:33]>C(OCC)(=O)C.CN1CCCC1=O>[C:32]([C:34]1[CH:66]=[CH:65][CH:64]=[CH:63][C:35]=1[O:36][C:37]1[C:51]([O:52][C:53]2[CH:54]=[CH:55][C:56]([S:59]([CH3:62])(=[O:60])=[O:61])=[CH:57][CH:58]=2)=[CH:50][C:40]2[NH:41][C:7]([C:3]3[N:2]=[N:1][CH:6]=[CH:5][CH:4]=3)=[N:43][C:39]=2[CH:38]=1)#[N:33]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 269369Pyridazine-3-carboxylic acidHCID 231451485-(2-Cyano-phenoxy)-2-pyridin-2-yl-6-(4-methanesulfonyl-phenoxy)-1H-benzimidazoleHCID 866192011-(3-Dimethylaminopropyl)-3-ethylcarbodiimide monohydride

생성물 1

HCID 231456775-(2-Cyano-phenoxy)-2-pyridazin-3-yl-6-(4-methanesulfonyl-phenoxy)-1H-benzimidazole

시약·촉매·용매

2
HCID 8857Ethyl Acetate용매HCID 13387N-methyl-2-pyrrolidone용매

실험 절차

3.3 mg of pyridazine-3-carboxylic acid, 15 mg of 1-hydroxybenzotriazole and 15 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide monohydride were added in order to an N-methylpyrrolidone (0.3 ml) solution of 15 mg of 4-(2-cyano-phenoxy)-5-(4-methanesulfonyl-phenoxy)-benzene-1,2-diamine obtained in Example 17, and the reaction liquid was stirred overnight at room temperature. The reaction liquid was diluted with ethyl acetate, and washed with saturated sodium bicarbonate solution, and the solvent was evaporated away under reduced pressure. The resulting residue was dissolved in 0.2 ml of N-methylpyrrolidone, and 5 mg of ytterbium trifluoromethanesulfonate was added to it, and the reaction liquid was stirred overnight at 140° C. The reaction mixture was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid]. The solvent of the resulting fraction was evaporated away under reduced pressure to obtain the entitled compound as a brown solid.

후처리

  1. customthe reaction liquid
  2. customThe reaction liquid
  3. washwashed with saturated sodium bicarbonate solution
  4. customthe solvent was evaporated away under reduced pressure
  5. dissolutionThe resulting residue was dissolved in 0.2 ml of N-methylpyrrolidone
  6. addition5 mg of ytterbium trifluoromethanesulfonate was added to it
  7. customthe reaction liquid
  8. stirringwas stirred overnight at 140° C
  9. customThe reaction mixture was purified through reversed-phase middle-pressure liquid chromatography [ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid]
  10. customThe solvent of the resulting fraction was evaporated away under reduced pressure

출처 및 근거

ORD 기록
ord-5774c958750448d2b4d40f2b1deb96a8
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07728025B2

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