Hydrochloric Acid → HCID 54739214, compound

HRID 2046280Notes

Reaction equation

HRID 2046280 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]1[C:16](=[O:17])[C:15]([C:18](OCC)=[O:19])=[C:14]([OH:23])[C:13]([CH:24]([CH3:26])[CH3:25])=[N:12]1.[H-].[Na+].BrCC1SC2C=CC=CC=2[N:35]=1.Cl.CC[O:43][C:44]([CH3:46])=[O:45]>CN(C)C=O.O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]1[C:16](=[O:17])[C:15]([C:18]([NH:35][CH2:46][C:44]([OH:43])=[O:45])=[O:19])=[C:14]([OH:23])[C:13]([CH:24]([CH3:26])[CH3:25])=[N:12]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 27762582-(Bromomethyl)-1,3-benzothiazoleHCID 68812129HCID 68812129, compound

Product 1

HCID 54739214HCID 54739214, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Ethyl 2-(1,3-benzothiazol-2-ylmethyl)-5-hydroxy-6-(1-methylethyl)-3-oxo-2,3-dihydro-4-pyridazinecarboxylate. Sodium hydride (53 mg, 1.326 mmol) was added to a solution of the compound from example 14a) (120 mg, 0.530 mmol) in N,N-Dimethylformamide (DMF) (3 ml) at 0° C. The reaction was brought to room temperature and stirred for 40 minutes. The temperature was then reduced to 0° C. and 2-(bromomethyl)-1,3-benzothiazole (112 mg, 0.491 mmol) was added. The reaction was brought to room temperature and stirred for 3 h followed by the addition of 1N HCl. The solution was diluted with EtOAc and H2O and the layers separated. The aqueous layer was backextracted with EtOAc several times. The combined organic layers were washed with Brine, dried (MgSO4), filtered and concentrated. The product was purified by column chromatography (SiO2, 35-60% EtOAc/Hexanes) to give the title compound as an orange oil (61 mg, 0.163 mmol, 31%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.48 (s, 1H) 8.05-8.11 (m, 1H) 7.97-8.02 (m, 1H) 7.52 (ddd, J=8.21, 7.20, 1.26 Hz, 1H) 7.44 (td, J=7.58, 1.26 Hz, 1H) 5.59 (s, 2H) 4.27 (q, J=7.07 Hz, 2H) 3.20 (sept, J=6.82 Hz, 1H) 1.26 (t, J=7.20 Hz, 3H) 1.19 (d, J=6.82 Hz, 6H).

Workup

  1. customwas brought to room temperature
  2. customwas then reduced to 0° C.
  3. customwas brought to room temperature
  4. stirringstirred for 3 h
  5. customthe layers separated
  6. washThe combined organic layers were washed with Brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe product was purified by column chromatography (SiO2, 35-60% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-c7b535085ba645a9a51b75b81a11f437
Source dataset
uspto-grants-2013_11
Patent number
USRE044613E1

Reaction notes

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