HCID 71062654, compound → HCID 71062169, compound

HRID 529005Notes

Reaction equation

HRID 529005 reaction equation
[CH2:1]([N:5]([CH2:47][CH2:48][CH2:49][CH3:50])[C:6]([C:8]1[N:9]=[C:10]([C:19]2[CH:34]=[CH:33][C:22]([C:23]([O:25]CC3C=CC=CC=3)=[O:24])=[CH:21][C:20]=2[C:35]([N:37]2[CH2:46][CH2:45][C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH2:38]2)=[O:36])[N:11]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:12]=1)=[O:7])[CH2:2][CH2:3][CH3:4]>CO.[Pd]>[CH2:47]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]([C:8]1[N:9]=[C:10]([C:19]2[CH:34]=[CH:33][C:22]([C:23]([OH:25])=[O:24])=[CH:21][C:20]=2[C:35]([N:37]2[CH2:46][CH2:45][C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH2:38]2)=[O:36])[N:11]([CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:12]=1)=[O:7])[CH2:48][CH2:49][CH3:50]

Participants

4

Reactant 1

HCID 71062654HCID 71062654, compound

Product 1

HCID 71062169HCID 71062169, compoundYield 89.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl 4-(4-(dibutylcarbamoyl)-1-(2-ethoxy-2-oxoethyl)-1H-imidazol-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (250 mg, 0.36 mmol) in MeOH (5.0 mL) was added Pd/C (10%). The resulting reaction mixture was stirred under H2 atmosphere for 2 h. The reaction mixture was filtered through a small pad of CELITE®, washed thoroughly with MeOH and concentrated in vacuo to provide the title compound (190 mg, 88%). 1H NMR (DMSO-d6, 1:1 mixture of amide rotamers) δ 13.4 (br s, 1H), 8.07 (d, J=8.0 Hz, 1H), 7.94 (d, J=9.6 Hz, 1H), 7.71 (s, 0.5H), 7.65 (s, 0.5H), 7.50 (t, J=8.6 Hz, 1H), 7.19-7.08 (m, 3.5H), 6.95 (d, J=7.6 Hz, 0.5H), 4.93 (br s, 2H), 4.63 (br s, 1H), 4.40-4.30 (br s, 1H), 4.15 (q, J=14.0, 6.8 Hz, 2H), 3.68 (br s, 2H), 3.46-3.42 (m, 2H), 3.30-3.20 (m, 2H), 2.74-2.62 (m, 2H), 1.44-1.27 (m, 4H), 1.22-1.20 (m, 3H), 1.19-1.16 (m, 4H), 0.95-0.72 (m, 6H); MS(ESI+) m/z 589.6 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. filtrationThe reaction mixture was filtered through a small pad of CELITE®
  3. washwashed thoroughly with MeOH
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eaa4e94bba3a4dd193d26e119f6c7400
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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