Hydrochloric Acid → HCID 57893430, compound

HRID 2046253Notes

Reaction equation

HRID 2046253 reaction equation
[OH:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[N:6][N:5]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:4](=[O:19])[C:3]=1[C:20](OCC)=[O:21].[H-].[Na+].OC1C(C(F)(F)F)=NNC(=O)[C:29]=1[C:39]([O:41]CC)=[O:40].C(Br)C1C=CC=CC=1.Cl.C[N:54](C)C=O>>[OH:1][C:2]1[C:7]([C:8]([F:10])([F:11])[F:9])=[N:6][N:5]([CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:4](=[O:19])[C:3]=1[C:20]([NH:54][CH2:29][C:39]([OH:41])=[O:40])=[O:21]

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 68812564HCID 68812564, compoundHCID 68813589HCID 68813589, compound

Product 1

HCID 57893430HCID 57893430, compoundYield 44%

Procedure

Ethyl 5-hydroxy-3-oxo-2-(phenylmethyl)-6-(trifluoromethyl)-2,3-dihydro-4-pyridazinecarboxylate. Sodium hydride (0.040 g of a 60% oil suspension, 1.00 mmol) was added to a stirred solution of ethyl 5-hydroxy-3-oxo-6-(trifluoromethyl)-2,3-dihydro-4-pyridazinecarboxylate (0.083 g, 0.329 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 (0.043 mL, 0.362 mmol) injected. The mixture was stirred for 3 h at 0° C. 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, 5-10% methanol dichloromethane) to give the title compound (0.050 g, 44%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.23 (t, J=6.95 Hz, 3H) 4.17 (q, J=7.07 Hz, 2H) 5.14 (s, 2H) 7.12-7.44 (m, 5H).

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. stirringThe mixture was stirred for 3 h at 0° C
  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, 5-10% methanol dichloromethane)

Sources & evidence

ORD record
ord-b660b3ec97ec4a27b6ce00014e62450d
Source dataset
uspto-grants-2013_11
Patent number
USRE044613E1

Reaction notes

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