Hydrochloric Acid → HCID 69413378, compound

HRID 25824Notes

Reaction equation

HRID 25824 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 (cone.). 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-679a1d124e6a4317b11c83bd669cc913
Source dataset
uspto-grants-2005_02
Patent number
US06858600B2

Reaction notes

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