HCID 66606939, compound → HCID 46834379, compound

HRID 1811094Notes

Reaction equation

HRID 1811094 reaction equation
[C:1]1([C:7]2[CH:19]=[CH:18][C:17]([C:20]([NH2:22])=[O:21])=[C:16]3[C:8]=2[C:9]2[CH2:10][CH2:11][CH:12]([C:23]([NH:25][CH:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)=[O:24])[CH2:13][C:14]=2[NH:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1>CO.[Pd]>[CH:1]1([C:7]2[CH:19]=[CH:18][C:17]([C:20]([NH2:22])=[O:21])=[C:16]3[C:8]=2[C:9]2[CH2:10][CH2:11][CH:12]([C:23]([NH:25][CH:26]4[CH2:27][CH2:28][O:29][CH2:30][CH2:31]4)=[O:24])[CH2:13][C:14]=2[NH:15]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 66606939HCID 66606939, compound

Product 1

HCID 46834379HCID 46834379, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 5-cyclohexenyl-N2-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carbazole-2,8-dicarboxamide (Example 3-117, 28 mg, 0.066 mmol) in methanol (10 mL) was combined with 10% palladium on charcoal (80 mg) and shaken under an atmosphere of hydrogen (45 psi) for 1 h. The mixture was filtered, the solid was rinsed with methanol and the filtrates were concentrated to provide 5-cyclohexyl-N2-(tetrahydro-2H-pyran-4-yl)-2,3,4,9-tetrahydro-1H-carbazole-2,8-dicarboxamide as an off-white solid (28 mg, quantitative). 1H NMR (400 MHz, methanol-d4) δ 7.46-7.50 (1H, m), 6.91 (1H, d, J=8.05 Hz), 3.89-3.98 (3H, m), 3.46-3.54 (2H, m), 3.13 (1H, dd, J=14.43, 4.16 Hz), 2.95-3.06 (2H, m), 2.87-2.94 (1H, m), 2.65-2.73 (1H, m), 2.15 (1H, dd, J=11.10, 3.05 Hz), 1.77-1.99 (8H, m), 1.47-1.61 (6H, m), 1.26-1.40 (2H, m). Mass spectrum m/z 424.3 (M+H)+.

Workup

  1. filtrationThe mixture was filtered
  2. washthe solid was rinsed with methanol
  3. concentrationthe filtrates were concentrated

Sources & evidence

ORD record
ord-91efb34c74a940b891e061af0c95a2f8
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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