HCID 11720214, compound → HCID 11703265, compound

HRID 1432423Notes

Reaction equation

HRID 1432423 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[NH:18][C:19]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([CH3:37])[N:32]=3)=[C:20]([C:22]3[CH:30]=[CH:29][C:25]4[O:26][CH2:27][O:28][C:24]=4[CH:23]=3)[N:21]=2)[CH2:13][CH2:12]1)=O)C1C=CC=CC=1>[Pd].CO>[O:26]1[C:25]2[CH:29]=[CH:30][C:22]([C:20]3[N:21]=[C:17]([CH:14]4[CH2:13][CH2:12][NH:11][CH2:16][CH2:15]4)[NH:18][C:19]=3[C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([CH3:37])[N:32]=3)=[CH:23][C:24]=2[O:28][CH2:27]1

Participants

4

Reactant 1

HCID 11720214HCID 11720214, compound

Product 1

HCID 11703265HCID 11703265, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on activated carbon (0.010 g) was added to a solution of 4-(4-benzo[1,3]dioxol-5-yl-5-(6-methyl-pyridin-2-yl)-1H-imidazol-2-yl)-piperidine-1-carboxylic acid benzyl ester (0.100 g, 0.20 mmol; see Example 5) in methanol (5 mL). The reaction mixture was stirred under hydrogen atmosphere for 4 hours. The mixture was then filtered and concentrated to give 0.070 g (97%) of the title compound as a yellow oil. MS (ESP+) m/z 363.2 (M+1). 1H NMR (300 MHz, CDCl3) δ 7.41 (t, 1H, J=7.8 Hz), 7.29 (d, 1H, J=8.1 Hz), 7.10 (m, 2H), 6.92 (d, 1H, J=7.5 Hz), 6.83 (m, 1H), 5.98 (s, 2H), 3.18 (m, 2H), 2.95 (m, 1H), 2.73 (m, 2H), 2.46 (s, 3H), 1.96 (m, 2H), 1.82 (m, 2H).

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-6788ba4fdd92455191eaebfaa4df976c
Source dataset
uspto-grants-2009_11
Patent number
US07612094B2

Reaction notes

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