3,4-Dichlorophenyl isocyanate → HCID 46235173, compound

HRID 407157Notes

Reaction equation

HRID 407157 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[C:15]3[C:11]([C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:13][NH:14]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[Cl:22][C:23]1[CH:24]=[C:25]([N:30]=[C:31]=[O:32])[CH:26]=[CH:27][C:28]=1[Cl:29].C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>O1CCCC1>[Cl:22][C:23]1[CH:24]=[C:25]([NH:30][C:31](=[O:32])[NH:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[CH:16]=[C:15]4[C:11]([C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:13][NH:14]4)=[CH:10][CH:9]=3)=[CH:6][CH:7]=2)[CH:26]=[CH:27][C:28]=1[Cl:29]

Participants

6

Reactant 4

HCID 76073,4-Dichlorophenyl isocyanateHCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 53244426HCID 53244426, compound

Product 1

HCID 46235173HCID 46235173, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The mixture of ethyl 6-(4-aminophenyl)-1H-indazole-3-carboxylate (40 mg) and 3,4-dichlorophenylisocyanate in tetrahydrofuran (3 Ml; THF) was stirred at room temperature for 24 h. Ethyl acetate and saturated sodium bicarbonate solution were wadded. The aqueous layer was extracted with ethyl acetate and the combined organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was triturated by THF/hexane to give ethyl 6-(4-(3-(3,4-dichlorophenyl)ureido)phenyl)-1H-indazole-3-carboxylate (17.4 mg).

Workup

  1. extractionThe aqueous layer was extracted with ethyl acetate
  2. dry with materialthe combined organic layer was dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was triturated by THF/hexane

Sources & evidence

ORD record
ord-50c5792a91164ae492d628814f5bfdfb
Source dataset
uspto-grants-2014_06
Patent number
US08754209B2

Reaction notes

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