Methanol → HCID 21079217, compound

HRID 730186Notes

Reaction equation

HRID 730186 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]=[O:12])=[CH:6][CH:5]=1)[CH3:2].[NH2:13][C:14]1[C:22]2[C:17](=[CH:18][C:19]([Cl:29])=[C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:21]=2)[N:16](COCC[Si](C)(C)C)[N:15]=1.OP([O-])(O)=O.[K+].CO>C1COCC1>[Cl:29][C:19]1[CH:18]=[C:17]2[C:22]([C:14]([NH:13][C:11]([NH:10][C:7]3[CH:8]=[CH:9][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=3)=[O:12])=[N:15][NH:16]2)=[CH:21][C:20]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 122887Benzene, 1-ethoxy-4-isocyanato-HCID 516951Monobasic potassium phosphateHCID 21079252HCID 21079252, compound

Product 1

HCID 21079217HCID 21079217, compoundYield 71.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

36.4 mg of 4-ethoxyphenyl isocyanate are added to 80 mg of 3-amino-5-phenyl-6-chloro-1-[(2-trimethylsilylethoxy)methyl]indazole in 1 ml of THF. The mixture is heated at 50° C. for 1 h and is then hydrolyzed in a saturated KH2PO4 solution and extracted with methylene chloride. After drying and evaporating, the crude product is purified by chromatography on silica with an AcOEt/hexane mixture. The product obtained is deprotected in 2 ml of a 1/1 MeOH/2N HCL mixture at reflux for 3 h. 62.5 mg of 1-(6-chloro-5-phenyl-1H-indazol-3-yl)-3-(4-ethoxyphenyl)urea are obtained.

Workup

  1. extractionextracted with methylene chloride
  2. customAfter drying
  3. customevaporating
  4. customthe crude product is purified by chromatography on silica with an AcOEt/hexane mixture
  5. customThe product obtained
  6. temperatureat reflux for 3 h

Sources & evidence

ORD record
ord-d65792988baf47fb8c2b265acf5030b7
Source dataset
uspto-grants-2009_09
Patent number
US07582669B2

Reaction notes

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