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

HRID 13240
Notes
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Reaction equation

HRID 13240 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5774c958750448d2b4d40f2b1deb96a8
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07728025B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes