Hydrochloric Acid → HCID 57893419, compound

HRID 1822381Notes

Reaction equation

HRID 1822381 reaction equation
[CH:1]1([C:7]2[C:8]([OH:26])=[C:9]([C:21](OCC)=[O:22])[C:10](=[O:20])[N:11]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].C1(C2C(O)=[C:37]([C:42]([O:44]CC)=[O:43])C(=O)NN=2)CCCCC1.C(Br)C1C=CC=CC=1.Cl.C[N:58](C)C=O>>[CH:1]1([C:7]2[C:8]([OH:26])=[C:9]([C:21]([NH:58][CH2:37][C:42]([OH:44])=[O:43])=[O:22])[C:10](=[O:20])[N:11]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[N:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 54693618HCID 54693618, compoundHCID 68814849HCID 68814849, compound

Product 1

HCID 57893419HCID 57893419, compoundYield 71%

Procedure

Ethyl 6-cyclohexyl-5-hydroxy-3-oxo-2-(phenylmethyl)-2,3-dihydro-4-pyridazinecarboxylate. Sodium hydride (0.040 g of a 60% oil suspension, 1.00 mmol) was added to a stirred suspension of ethyl 6-cyclohexyl-5-hydroxy-3-oxo-2,3-dihydro-4-pyridazinecarboxylate (0.100 g, 0.376 mmol) in dimethylformamide (1.5 mL) under nitrogen. After 10 min stirring at room temperature, the mixture was cooled in an ice bath and benzyl bromide (0.045 mL, 0.378 mmol) injected. The mixture was stirred for 0.5 h at 0° C. and 0.5 h at room temperature. 0.1M aqueous hydrochloric acid (50 mL) was added and the mixture extracted with ethyl acetate. The extracts were washed with water and brine, then dried (MgSO4), evaporated under reduced pressure and the residue chromatographed (silica gel, 0-4% methanol/dichloromethane) to give the title compound (0.095 g, 71%) as a colourless oil. LCMS (ES+) m/z 357 (MH+).

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. stirringThe mixture was stirred for 0.5 h at 0° C. and 0.5 h at room temperature
  3. extractionthe mixture extracted with ethyl acetate
  4. washThe extracts were washed with water and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure
  7. customthe residue chromatographed (silica gel, 0-4% methanol/dichloromethane)

Sources & evidence

ORD record
ord-b20d574e12974d4790cc741fe448e189
Source dataset
uspto-grants-2009_10
Patent number
US07608621B2

Reaction notes

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