HCID 86657833, compound → HCID 86657832, compound

HRID 402066Notes

Reaction equation

HRID 402066 reaction equation
[N:1]([CH2:4][C@H:5]1[CH2:10][CH2:9][N:8]([C:11]([C:13]2[N:14]=[N:15][C:16]([CH2:32][CH2:33][CH2:34][CH3:35])=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH:26]4[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]4)=[CH:21][CH:20]=3)[CH:18]=2)=[O:12])[CH2:7][C@H:6]1[O:36][CH3:37])=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][C@H:5]1[CH2:10][CH2:9][N:8]([C:11]([C:13]2[N:14]=[N:15][C:16]([CH2:32][CH2:33][CH2:34][CH3:35])=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH:26]4[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]4)=[CH:21][CH:20]=3)[CH:18]=2)=[O:12])[CH2:7][C@H:6]1[O:36][CH3:37]

Participants

4

Reactant 1

HCID 86657833HCID 86657833, compound

Product 1

HCID 86657832HCID 86657832, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of (±)-cis-(4-azidomethyl-3-methoxy-piperidin-1-yl)-[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yl]-methanone (0.23 mmol, 120 mg) in methanol (1 mL) was added Pd—C (20% by wt., 25 mg). The reaction was hydrogenated at room temperature under balloon pressure for 2.5 h. The reaction was filtered through celite, and the solvent removed under reduced pressure to provide (±)-cis-(4-aminomethyl-3-methoxy-piperidin-1-yl)-[6-butyl-5-(4-cyclohexyloxy-phenyl)-pyridazin-3-yl]-methanone.

Workup

  1. filtrationThe reaction was filtered through celite
  2. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-4e040b6accc2434e8c8afb65843304fd
Source dataset
uspto-grants-2014_06
Patent number
US08741900B2

Reaction notes

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