HCID 68432003, compound → HCID 68430610, compound

HRID 2092092Notes

Reaction equation

HRID 2092092 reaction equation
[F:1][CH:2]([F:28])[O:3][C:4]1[C:5](=[O:27])[N:6](C2CCCCO2)[N:7]=[CH:8][C:9]=1[NH:10][C@@H:11]1[CH2:16][C@@H:15]2[CH2:17][C@@H:13]([C:14]2([CH3:19])[CH3:18])[C@H:12]1[CH3:20]>C(O)(=O)C.O1CCCC1.O.Cl>[F:28][CH:2]([F:1])[O:3][C:4]1[C:5](=[O:27])[NH:6][N:7]=[CH:8][C:9]=1[NH:10][C@@H:11]1[CH2:16][C@@H:15]2[CH2:17][C@@H:13]([C:14]2([CH3:19])[CH3:18])[C@H:12]1[CH3:20]

Participants

4

Reactant 1

HCID 68432003HCID 68432003, compound

Product 1

HCID 68430610HCID 68430610, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 21877175AcOH THF waterSolvent

Procedure

4-Difluoromethoxy-2-(tetrahydro-2H-pyran-2-yl)-5-{[(1R,2R,3R,5S)-2,6,6-trimethylbicyclo[3.1.1]hept-3-yl]amino}pyridazin-3(2H)-one (80 mg, 0.20 mmol) in acetic acid-tetrahydrofuran-water (5/1/1) was stirred at 90° C. for 3 hours and then stirred with two drops of concentrated hydrochloric acid for another 3 hours. After completion of the reaction, the reaction solution was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1 to 1/1) to give the desired product (48 mg, 79% yield).

Workup

  1. customAfter completion of the reaction
  2. customthe reaction solution was evaporated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1 to 1/1)

Sources & evidence

ORD record
ord-5cd9872d18374226be5908a9efb75f6a
Source dataset
uspto-grants-2013_05
Patent number
US08440666B2

Reaction notes

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