Cesium carbonate → HCID 86654080, compound

HRID 521004Notes

Reaction equation

HRID 521004 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:17]2[C@@H:12]([C:13]3[C:21]([OH:22])=[CH:20][CH:19]=[CH:18][C:14]=3[CH2:15][CH2:16]2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:24]1[N:25]=[N:26][C:27]([CH3:30])=[CH:28][CH:29]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN1CCCC1=O>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C@@H:17]2[C@@H:12]([C:13]3[C:21]([O:22][C:24]4[N:25]=[N:26][C:27]([CH3:30])=[CH:28][CH:29]=4)=[CH:20][CH:19]=[CH:18][C:14]=3[CH2:15][CH2:16]2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 13387N-methyl-2-pyrrolidoneHCID 2272543-Chloro-6-methylpyridazineHCID 86654078HCID 86654078, compound

Product 1

HCID 86654080HCID 86654080, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of cis-10-hydroxy-2,3,4a,5,6,10b-hexahydro-1H-benzo[f]quinoline-4-carboxylic acid tert-butyl ester (0.40 g), 3-chloro-6-methyl-pyridazine (0.13 g), cesium carbonate (0.35 g), and N-methylpyrrolidinone (5 mL) is stirred at 150° C. for 1.5 h. After cooling to room temperature, the mixture is diluted with ethyl acetate and washed with water and brine and dried (Na2SO4). The solvent is evaporated and the residue is chromatographed on silica gel (cyclohexane/ethyl acetate 3:1→1:2) to give the title compound. Yield: 0.14 g (impure); LC (method 1): tR=4.19 min; Mass spectrum (ESI+): m/z=396 [M+H]+.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water and brine
  3. dry with materialdried (Na2SO4)
  4. customThe solvent is evaporated
  5. customthe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 3:1→1:2)

Sources & evidence

ORD record
ord-1837e2ea97e6429bae5d6bb2ea9b9eca
Source dataset
uspto-grants-2016_05
Patent number
US09328072B2

Reaction notes

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