Hydrochloric Acid → HCID 57893420, compound

HRID 2046255Notes

Reaction equation

HRID 2046255 reaction equation
[CH:1]1([C:7]2[C:8]([OH:30])=[C:9]([C:25](OCC)=[O:26])[C:10](=[O:24])[N:11]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]([CH3:23])([CH3:22])[CH3:21])=[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:41]([C:46]([O:48]CC)=[O:47])C(=O)NN=2)CCCCC1.C(C1C=CC(CBr)=CC=1)(C)(C)C.Cl.C[N:66](C)C=O>>[CH:1]1([C:7]2[C:8]([OH:30])=[C:9]([C:25]([NH:66][CH2:41][C:46]([OH:48])=[O:47])=[O:26])[C:10](=[O:24])[N:11]([CH2:13][C:14]3[CH:15]=[CH:16][C:17]([C:20]([CH3:22])([CH3:21])[CH3:23])=[CH:18][CH:19]=3)[N:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 54693618HCID 54693618, compoundHCID 68811893HCID 68811893, compound

Product 1

HCID 57893420HCID 57893420, compoundYield 56%

Procedure

Ethyl 6-cyclohexyl-2-{[4-(1,1-dimethylethyl)phenyl]methyl}-5-hydroxy-3-oxo-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 (example 10(a), 0.100 g, 0.376 mmol) in dimethylformamide (2.0 mL) under nitrogen. After 15 min stirring at room temperature, the mixture was cooled in an ice bath and 4-tert-butylbenzyl bromide (0.071 mL, 0.384 mmol) injected. The mixture was stirred for 0.5 h at 0° C. and 3 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 dilute aqueous sodium chloride, then dried (MgSO4), evaporated under reduced pressure and the residue chromatographed (silica gel, 0-6% methanol/dichloromethane) to give the title compound (0.087 g, 56%) as a gum. LCMS (ES+) m/z 413 (MH+).

Workup

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

Sources & evidence

ORD record
ord-175a439f0bb94d03a465f88e8b555e31
Source dataset
uspto-grants-2013_11
Patent number
USRE044613E1

Reaction notes

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