Hydrochloric Acid → HCID 17984293, compound

HRID 1869233Notes

Reaction equation

HRID 1869233 reaction equation
[CH2:1]([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])[CH3:2].[CH3:8][CH:9]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([C:20]([Cl:22])=[O:21])=[N:12]1)[CH3:10].[OH2:23].Cl>CN(C=O)C.C(O)C>[ClH:22].[OH:23][C:14]1[CH:19]=[CH:18][C:17]([CH2:2][CH2:1][N:3]2[CH2:6][CH2:7][CH:8]([CH2:9][NH:11][C:20]([C:13]3[C:14]4[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=4)[N:11]([CH:9]([CH3:10])[CH3:8])[N:12]=3)=[O:21])[CH2:5][CH2:4]2)=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8471TriethylamineHCID 21252895HCID 21252895, compound

Product 1

HCID 17984293HCID 17984293, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent2×

Procedure

A solution of the product obtained in step 1b) (10.0 g, 0.043 moles) and triethyl-amine (30 ml, 0.21 moles) in DMF (100 ml) was added dropwise to a solution of 1-(1-methylethyl)-1H-indazole-3-carboxylic acid chloride (9.5 g, 0.043 moles), prepared as described in EP-A-0 975 623, in DMF (50 ml). After having been stirred continuously at room temperature for 18 hrs, the reaction mixture was transferred into a separatory funnel, added with H2O, and extracted with ethyl acetate (3×150 ml). The organic phase was separated and dried over Na2SO4. The solvent was removed by evaporation under reduced pressure. The residue thus obtained was taken up with absolute ethanol and transformed into the corresponding hydrochloride salt by addition of ethanolic hydrogen chloride. The solution was evaporated under reduced pressure and the residue was crystallised from ethanol to give the desired product (20 g).

Workup

  1. customprepared
  2. customthe reaction mixture was transferred into a separatory funnel
  3. extractionextracted with ethyl acetate (3×150 ml)
  4. customThe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed by evaporation under reduced pressure
  7. customThe residue thus obtained
  8. customThe solution was evaporated under reduced pressure
  9. customthe residue was crystallised from ethanol

Sources & evidence

ORD record
ord-9a5621813b9e4ec5b8dbc154b03e98e8
Source dataset
uspto-grants-2009_12
Patent number
US07638534B2

Reaction notes

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