HCID 71272547, compound → HCID 68014668, compound

HRID 1528062Notes

Reaction equation

HRID 1528062 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([N:15]2[CH:19]=[C:18]([F:20])[C:17]([F:21])=[CH:16]2)[CH:12]=[CH:11][C:10]=1[N:22]1[CH:27]=[C:26]([O:28][CH3:29])[C:25](=[O:30])[C:24]([C:31]2[N:35]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:34]=[CH:33][CH:32]=2)=[N:23]1)C1C=CC=CC=1>[Pd].C(O)(=O)C>[F:21][C:17]1[C:18]([F:20])=[CH:19][N:15]([C:13]2[CH:12]=[CH:11][C:10]([N:22]3[CH:27]=[C:26]([O:28][CH3:29])[C:25](=[O:30])[C:24]([C:31]4[N:35]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[N:34]=[CH:33][CH:32]=4)=[N:23]3)=[C:9]([OH:8])[CH:14]=2)[CH:16]=1

Participants

4

Reactant 1

HCID 71272547HCID 71272547, compound

Product 1

HCID 68014668HCID 68014668, compoundYield 46.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A suspension of 1-[2-(benzyloxy)-4-(3,4-difluoro-1H-pyrrol-1-yl)phenyl]-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (3.20 g) and 10% palladium on carbon (containing water (50%), 3.20 g) in acetic acid (100 mL) was stirred at room temperature for 3 hr under a hydrogen atmosphere. The palladium on carbon was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by SFC (column: CHIRALPAK ADH (trade name), 20 mmID×250 mL, manufactured by DAICEL CHEMICAL INDUSTRIES, LTD., mobile phase: carbon dioxide/2-propanol/acetonitrile=700/150/150 (v/v/v)), and the obtained fraction was concentrated under reduced pressure. The residue was recrystallized from acetone to give the title compound (1.24 g).

Workup

  1. customThe palladium on carbon was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by SFC (column: CHIRALPAK ADH (trade name), 20 mmID×250 mL, manufactured by DAICEL CHEMICAL INDUSTRIES, LTD., mobile phase: carbon dioxide/2-propanol/acetonitrile=700/150/150 (v/v/v))
  4. concentrationthe obtained fraction was concentrated under reduced pressure
  5. customThe residue was recrystallized from acetone

Sources & evidence

ORD record
ord-1de8132569e0462e835f5f044e68ff58
Source dataset
uspto-grants-2015_07
Patent number
US09090586B2

Reaction notes

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