Hydrochloric Acid → HCID 57893421, compound

HRID 2046251Notes

Reaction equation

HRID 2046251 reaction equation
[CH:1]1([CH2:4][CH2:5][N:6]2[C:11](=[O:12])[C:10]([C:13](OCC)=[O:14])=[C:9]([OH:18])[C:8]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[N:7]2)[CH2:3][CH2:2]1.[H-].[Na+].OC1C(C2C=CC=CC=2)=NNC(=O)[C:29]=1[C:41]([O:43]CC)=[O:42].BrCCC1CC1.Cl.C[N:54](C)C=O>>[CH:1]1([CH2:4][CH2:5][N:6]2[C:11](=[O:12])[C:10]([C:13]([NH:54][CH2:29][C:41]([OH:43])=[O:42])=[O:14])=[C:9]([OH:18])[C:8]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[N:7]2)[CH2:2][CH2:3]1

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 22636989(2-Bromoethyl)cyclopropaneHCID 68812076HCID 68812076, compoundHCID 68812286HCID 68812286, compound

Product 1

HCID 57893421HCID 57893421, compoundYield 53%

Procedure

Ethyl 2-(2-cyclopropylethyl)-5-hydroxy-3-oxo-6-phenyl-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-phenyl-2,3-dihydro-4-pyridazinecarboxylate (example 4(b), 0.100 g, 0.384 mmol) in dimethylformamide (1.5 mL) under nitrogen. After 15 min stirring at room temperature, the mixture was cooled in an ice bath and (2-bromoethyl)cyclopropane (0.057 g, 0.384 mmol) added. The mixture was stirred for 18 h while warming to room temperature, then poured into 0.1M aqueous hydrochloric acid (50 mL) and 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, 1-5% methanol/dichloromethane) to give the title compound (0.067 g, 53%) as a colourless gum. 1H NMR (400 MHz, DMSO-d6) δ ppm −0.05-0.06 (m, 2H) 0.34-0.45 (m, 2H) 0.64-0.78 (m, 1H) 1.29 (t, J=7.07 Hz, 3H) 1.62 (q, J=7.07 Hz, 2H) 4.14 (t, J=7.20 Hz, 2H) 4.31 (q, J=7.07 Hz, 2H) 7.41-7.52 (m, 3H) 7.63-7.71 (m, 2H) 12.42 (br. s., 1H).

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. stirringThe mixture was stirred for 18 h
  3. temperaturewhile warming to room temperature
  4. extractionextracted with ethyl acetate
  5. washThe extracts were washed with water and brine
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure
  8. customthe residue chromatographed (silica gel, 1-5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-5a1678fea5ea4e4f8f76e2c9b18ed17d
Source dataset
uspto-grants-2013_11
Patent number
USRE044613E1

Reaction notes

Loading…