(+/-)-trans-4-[6-Butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yloxy]-3-fluoro-piperidine-1-carboxylic acid benzyl ester → (+/-)-trans-3-Butyl-4-(4-cyclohexyloxy-phenyl)-6-(3-fluoro-piperidin-4-yloxy)-pyridazine

HRID 2168673Notes

Reaction equation

HRID 2168673 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][C@@H:14]([O:17][C:18]2[N:19]=[N:20][C:21]([CH2:37][CH2:38][CH2:39][CH3:40])=[C:22]([C:24]3[CH:29]=[CH:28][C:27]([O:30][CH:31]4[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]4)=[CH:26][CH:25]=3)[CH:23]=2)[C@H:13]([F:41])[CH2:12]1)=O)C1C=CC=CC=1>[Pd].CO>[CH2:37]([C:21]1[N:20]=[N:19][C:18]([O:17][C@@H:14]2[CH2:15][CH2:16][NH:11][CH2:12][C@H:13]2[F:41])=[CH:23][C:22]=1[C:24]1[CH:29]=[CH:28][C:27]([O:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)=[CH:26][CH:25]=1)[CH2:38][CH2:39][CH3:40]

Participants

4

Reactant 1

HCID 86657795(+/-)-trans-4-[6-Butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yloxy]-3-fluoro-piperidine-1-carboxylic acid benzyl ester

Product 1

HCID 86657796(+/-)-trans-3-Butyl-4-(4-cyclohexyloxy-phenyl)-6-(3-fluoro-piperidin-4-yloxy)-pyridazineYield 78%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (±)-trans-4-[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yloxy]-3-fluoro-piperidine-1-carboxylic acid benzyl ester (65 mg, 0.12 mmol) and 10% palladium on carbon (10 mg) in MeOH (5 mL) was stirred under an atmosphere of H2 for 1.5 hrs, filtered through celite and concentrated to provide (±)-trans-3-butyl-4-(4-cyclohexyloxy-phenyl)-6-(3-fluoro-piperidin-4-yloxy)-pyridazine (40 mg).

Workup

  1. filtrationfiltered through celite and
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-dcaba665890c41df9224b658703620f7
Source dataset
uspto-grants-2015_06
Patent number
US09045461B2

Reaction notes

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