Hydrochloric Acid → HCID 57893418, compound

HRID 2046256Notes

Reaction equation

HRID 2046256 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][N:9]1[C:14](=[O:15])[C:13]([C:16](OCC)=[O:17])=[C:12]([OH:21])[C:11]([CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[N:10]1.[H-].[Na+].C1(C2C(O)=[C:38]([C:43]([O:45]CC)=[O:44])C(=O)NN=2)CCCCC1.ClC1C=CC=CC=1CBr.Cl.C[N:60](C)C=O>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][N:9]1[C:14](=[O:15])[C:13]([C:16]([NH:60][CH2:38][C:43]([OH:45])=[O:44])=[O:17])=[C:12]([OH:21])[C:11]([CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[N:10]1

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 11905alpha-Bromo-o-chlorotolueneHCID 24758Sodium hydrideHCID 54693618HCID 54693618, compoundHCID 68812999HCID 68812999, compound

Product 1

HCID 57893418HCID 57893418, compoundYield 63%

Procedure

Ethyl 2-[(2-chlorophenyl)methyl]-6-cyclohexyl-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 2-chlorobenzyl bromide (0.051 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 (0.093 g, 63%) as a gum. LCMS (ES+) m/z 391 (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-977990e55d4c4de1b0644b0d2b70845e
Source dataset
uspto-grants-2013_11
Patent number
USRE044613E1

Reaction notes

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