Hydrochloric Acid → HCID 69413378, compound

HRID 971334Notes

Reaction equation

HRID 971334 reaction equation
[C:1]([CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]#[N:26])=[CH:19][C:18]=3[CH2:27][CH:28]([CH3:30])[CH3:29])=[CH:13][C:12]=2[CH:31]([CH3:33])[CH3:32])=[CH:7][C:6]=1[CH2:34][CH:35]([CH3:37])[CH3:36])#[N:2].[ClH:38]>CCO>[ClH:38].[ClH:38].[NH2:2][CH2:1][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][CH2:25][NH2:26])=[CH:19][C:18]=3[CH2:27][CH:28]([CH3:29])[CH3:30])=[CH:13][C:12]=2[CH:31]([CH3:33])[CH3:32])=[CH:7][C:6]=1[CH2:34][CH:35]([CH3:37])[CH3:36]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22565258HCID 22565258, compound

Product 1

HCID 69413378HCID 69413378, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-[4″-(cyanomethoxy)-2,3″-diisobutyl-3′-isopropyl-1,1′:4′,1″-terphenyl-4-yl]propanenitrile (8f) (19.0 mg, 0.038 mmol) was dissolved in 5 ml of EtOH containing 10% Pd/C (15 mg) and 0.1 ml HCl (conc.). The solution was stirred overnight under 20 psi of H2. The reaction mixture was filtered through celite and the filtrate was concentrated in vacuo to yield 20 mg of a white solid (91%): 1H NMR (500 MHz, CD3OD) δ 0.75 (d, J=6.6 Hz, 6H), 0.93 (d, J=6.9 Hz, 6H), 1.14 (d, J=6.9, 6H), 1.68 (m, 2H), 1.96 (m, 1H), 1.99 (m, 1H), 2.54 (d, J=6.6 Hz, 2H), 2.62 (d, J=6.9 Hz, 2H), 2.76 (t, J=7.4, 2H), 2.96 (t, J=6.8 Hz, 2H), 3.11 (m, 1H), 3.41 (t, J=4.5 Hz, 2H), 4.29 (t, J=5.0 Hz, 2H), 7.13 (m, 9H); 13C NMR (125 MHz, CD3OD) δ 22.85, 22.96, 24.61, 30.15, 30.53, 30.54, 30.81, 33.34, 40.12, 40.53, 40.70, 43.42, 66.06, 112.90, 126.84, 127.50, 127.67, 129.06, 130.75, 131.25, 131.29, 131.33, 133.29, 136.26, 140.46, 140.49, 140.59, 141.95, 142.56, 147.13, 156.52; HRMS (FAB, M+H) Calcd for C34H49N2O: 501.3845. Found 501.3845.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6137d790b6844c1db56a1b4e9738574e
Source dataset
uspto-grants-2007_12
Patent number
US07312246B2

Reaction notes

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