Trifluoroacetic acid → HCID 178449064, compound

HRID 528996Notes

Reaction equation

HRID 528996 reaction equation
[CH2:1]([N:5]([CH2:43][CH2:44][CH2:45][CH3:46])[C:6]([C:8]1[N:9]=[C:10]([C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=2[C:31]([N:33]2[CH2:42][CH2:41][C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:34]2)=[O:32])[N:11](COCC[Si](C)(C)C)[CH:12]=1)=[O:7])[CH2:2][CH2:3][CH3:4].FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:43]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]([C:8]1[N:9]=[C:10]([C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=2[C:31]([N:33]2[CH2:42][CH2:41][C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH2:34]2)=[O:32])[NH:11][CH:12]=1)=[O:7])[CH2:44][CH2:45][CH3:46]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 71062252Methyl 4-(4-(dibutylcarbamoyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate

Product 1

HCID 178449064HCID 178449064, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution methyl 4-(4-(dibutylcarbamoyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (180 mg, 0.28 mmol) in DCM (4 mL) was added trifluoroacetic acid (4 mL) at 0° C. The reaction mixture was allowed to warm to room temperature and stirring was continued for 4 h. The reaction mixture was concentrated in vacuo. The resulting residue was dissolved in DCM and washed with sat. NaHCO3 solution. The organic layer was dried over Na2SO4 and concentrated to give crude product. The crude material was purified by flash chromatography (gradient from 0 to 5% methanol/CHCl3) to provide the title compound (130 mg, 91%). 1H NMR (CD3OD) δ 8.25-8.06 (m, 2H), 8.00-7.50 (m, 2H), 7.28-6.83 (m, 4H), 4.36 (br s, 1H), 4.01 (br s, 4H), 3.60-3.24 (m, 6H), 2.88-2.69 (m, 2H), 1.60-1.52 (m, 4H), 1.36-1.30 (m, 4H), 1.05-0.90 (m, 6H); MS(ESI−) m/z 515.2 (M−H)−.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionThe resulting residue was dissolved in DCM
  3. washwashed with sat. NaHCO3 solution
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. customto give crude product
  7. customThe crude material was purified by flash chromatography (gradient from 0 to 5% methanol/CHCl3)

Sources & evidence

ORD record
ord-e2460e09de5942c790bc1da60c1f4e89
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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