HCID 178436210, compound → HCID 178436211, compound

HRID 2174054Notes

Reaction equation

HRID 2174054 reaction equation
[CH3:1][C:2]1[C:3]([CH2:13][C:14]2[NH:18][C:17]3[CH:19]=[CH:20][C:21]([C:23]#[N:24])=[CH:22][C:16]=3[N:15]=2)=[C:4]2[C:8](=[C:9]([CH:11]=[CH2:12])[CH:10]=1)[NH:7][CH:6]=[CH:5]2>CCOC(C)=O.[Pd]>[CH2:11]([C:9]1[CH:10]=[C:2]([CH3:1])[C:3]([CH2:13][C:14]2[NH:18][C:17]3[CH:19]=[CH:20][C:21]([C:23]#[N:24])=[CH:22][C:16]=3[N:15]=2)=[C:4]2[C:8]=1[NH:7][CH:6]=[CH:5]2)[CH3:12]

Participants

4

Reactant 1

HCID 178436210HCID 178436210, compound

Product 1

HCID 178436211HCID 178436211, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-((5-methyl-7-vinyl-1H-indol-4-yl)methyl)-1H-benzo[d]imidazole-5-carbonitrile (11 mg, 0.035 mmol) in EtOAc (0.7 mL) was added Pd/C (5%, 3.75 mg) and the reaction was stirred at room temperature under hydrogen. After 10 minutes the reaction was filtered through Celite®, rinsing with EtOAc, and concentrated. The resulting residue was purified directly by RP-HPLC (HC-A) to provide the title compound. 1H NMR (TFA salt, 400 MHz, DMSO-d6) δ ppm 10.97 (br. s., 1H) 7.98 (s, 1H) 7.61 (d, J=8.34 Hz, 1H) 7.53 (d, J=8.34 Hz, 1H) 7.23 (t, J=2.78 Hz, 1H) 6.79 (s, 1H) 6.45 (dd, J=3.16, 1.89 Hz, 1H) 4.46 (s, 2H) 2.81 (q, J=7.58 Hz, 2H) 2.37 (s, 3H) 1.25 (t, J=7.45 Hz, 3H). HRMS calcd. for C20H18N4 (M+H)+ 315.1604. found 315.1609.

Workup

  1. filtrationAfter 10 minutes the reaction was filtered through Celite®
  2. washrinsing with EtOAc
  3. concentrationconcentrated
  4. customThe resulting residue was purified directly by RP-HPLC (HC-A)

Sources & evidence

ORD record
ord-b9fb5cbb1cb64e02b994f07757ede5ae
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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