HCID 11627625, compound → HCID 11696504, compound

HRID 1432431Notes

Reaction equation

HRID 1432431 reaction equation
C(OC(=O)[NH:10][CH: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)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[CH2:15][CH2:16][CH:11]([NH2:10])[CH2:12][CH2:13]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 11627625HCID 11627625, compound

Product 1

HCID 11696504HCID 11696504, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on activated carbon (0.017 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]-cyclohexyl}-carbamic acid benzyl ester (see Example 18; 0.370 g, 0.725 mmol) in methanol (5 mL). The reaction mixture was stirred under hydrogen atmosphere for 4 hours. The mixture was then filtered and concentrated to give 0.250 g (92%) of the title compound as a yellow oil. MS (ESP+) m/z 377.2 (M+1). 1H NMR (300 MHz, Methanol-d4) δ 7.80 (t, 1H, J=7.8 Hz), 7.36 (m, 2H), 7.01 (m, 3H), 6.07 (s, 2H), 3.47 (m, 1H), 3.32 (m, 1H), 2.29 (m, 2H), 2.03 (m, 4H), 1.90 (m, 2H).

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-d6f1ebe0225b4f54859aff80e80d5024
Source dataset
uspto-grants-2009_11
Patent number
US07612094B2

Reaction notes

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