Hydrochloric Acid → HCID 77230773, compound

HRID 402813Notes

Reaction equation

HRID 402813 reaction equation
Cl.[CH:2]([C:4]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH3:14])=[CH:10][CH:11]=2)[N:6]([C:15](OC(C)(C)C)=O)[N:5]=1)=[O:3].[CH2:22]1CCN2C(=NCCC2)C[CH2:23]1.ICCC>O1CCOCC1.CN(C=O)C>[CH3:14][O:13][C:9]1[CH:8]=[C:7]2[C:12]([C:4]([CH:2]=[O:3])=[N:5][N:6]2[CH2:15][CH2:22][CH3:23])=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 336431-IodopropaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 58823813HCID 58823813, compound

Product 1

HCID 77230773HCID 77230773, compoundYield 63.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 2 M HCl in dioxane (0.47 mL, 0.94 mmol) was added to a stirred, room temperature mixture of tert-butyl 3-formyl-6-methoxy-1H-indazole-1-carboxylate (50 mg, 0.18 mmol) in dioxane (1 mL) and the mixture was stirred at room temperature for 8 hours. It was concentrated and dried under vacuum. To the residue in DMF (1.0 mL), DBU (0.08 mL, 0.54 mmol) was added and the reaction mixture was stirred for 30 minutes. Then 1-iodopropane (0.09 mL, 0.90 mmol) was added and the solution was stirred for 16 hours at room temperature. The solvent was removed in vacuo and the residue was partitioned between ethyl acetate (20 mL) and saturated sodium bicarbonate (5 mL), washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure to give the title compound (25 mg, 63% crude yield).

Workup

  1. concentrationIt was concentrated
  2. customdried under vacuum
  3. stirringthe reaction mixture was stirred for 30 minutes
  4. stirringthe solution was stirred for 16 hours at room temperature
  5. customThe solvent was removed in vacuo
  6. customthe residue was partitioned between ethyl acetate (20 mL) and saturated sodium bicarbonate (5 mL)
  7. washwashed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5ed7ec9b8acd4d63983694963e7504a2
Source dataset
uspto-grants-2014_06
Patent number
US08742110B2

Reaction notes

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