Trifluoroacetic acid → HCID 25016721, compound

HRID 1785613Notes

Reaction equation

HRID 1785613 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:13][N:12]([N:14]([CH2:22][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)C(=O)CC(C)(C)C)[C:11](=[O:29])[N:10]2[CH2:30][CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)[CH:5]=[CH:6][C:7]=1[CH3:8].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([CH:9]2[CH2:13][N:12]([NH:14][CH2:22][C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)[C:11](=[O:29])[N:10]2[CH2:30][CH2:31][C:32]2[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=2)[CH:5]=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 68427745HCID 68427745, compound

Product 1

HCID 25016721HCID 25016721, compoundYield 104.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-{4-(3,4-dimethylphenyl)-3-[2-(4-methoxyphenyl)ethyl]-2-oxo-imidazolidin-1-yl}-3,3-dimethyl-N-pyridin-4-ylmethyl-butyramide (205 mg, 0.386 mmol) in CH2Cl2 (1.5 mL) is cooled in an ice bath and triethylsilane (0.129 mL, 0.81 mmol) is added, followed by trifluoroacetic acid (1.5 mL). The ice bath is removed and the reaction is stirred at ambient temperature for 2.5 hours. The reaction is concentrated to an oil, dissolved in ethyl acetate, and washed with 10% aqueous NaHCO3, and brine. The organic phase is dried (Na2SO4), treated with 2N HCl/ether (0.7 mL), and concentrated under reduced pressure. The solid which results is re-crystallized from dichloromethane/ether to afford 174 mg (76% yield) of the desired compound. 1H NMR (DMSO-d6) δ 8.92 (d, J=6.0 Hz, 2H), 8.21 (d, J=6.0 Hz, 2H), 7.14 (d, J=7.5 Hz, 1H), 7.00 (m, 4H), 6.82 (d, J=8.1 Hz, 2H), 4.38 (m, 3H), 3.74 (s, 3H), 3.72 (m, 1H), 3.44 (m, 1H), 3.14 (t, J=7.8 Hz, 1H), 2.68 (m, 1H), 2.52 (m, 1H), 2.24 (s, 3H), 2.20 (s, 3H). MS 431 (MH+). Anal. calcd. for C26H30N4O22HCl: C, 62.03, H, 6.41; N, 11.13. Found: C, 61.99, H, 6.41; N, 11.13.

Workup

  1. customThe ice bath is removed
  2. concentrationThe reaction is concentrated to an oil
  3. dissolutiondissolved in ethyl acetate
  4. washwashed with 10% aqueous NaHCO3, and brine
  5. dry with materialThe organic phase is dried (Na2SO4)
  6. additiontreated with 2N HCl/ether (0.7 mL)
  7. concentrationconcentrated under reduced pressure
  8. customThe solid which results
  9. customis re-crystallized from dichloromethane/ether

Sources & evidence

ORD record
ord-ee58c4eb028248dbac4fa8b5ddb7daab
Source dataset
uspto-grants-2009_03
Patent number
US07504517B2

Reaction notes

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