Trifluoroacetic acid → HCID 59694145, compound

HRID 899737Notes

Reaction equation

HRID 899737 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]([CH:39]1[C:48]2[N:47]=[CH:46][CH:45]=[CH:44][C:43]=2[CH2:42][CH2:41][CH2:40]1)[CH2:12][CH2:13][CH2:14][C:15]1[N:16](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:17]=[CH:18][N:19]=1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]([CH2:12][CH2:13][CH2:14][C:15]1[NH:16][CH:17]=[CH:18][N:19]=1)[CH:39]1[C:48]2[N:47]=[CH:46][CH:45]=[CH:44][C:43]=2[CH2:42][CH2:41][CH2:40]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 69177651HCID 69177651, compound

Product 1

HCID 59694145HCID 59694145, compoundYield 75.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1H-benzimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-[3-(1-trityl-1H-imidazol-2-yl)-propyl]-amine (101 mg, 0.161 mmol) in CH2Cl2 (1.6 mL) was added triethylsilane (0.38 mL, 2.4 mmol) followed by TFA (1.9 mL, 25 mmol), and the solution was stirred at room temperature for 21 h then concentrated in vacuo. The residue was dissolved in CH2Cl2 (15 mL) and washed with 1 N NaOH(aq) (10 mL). The aqueous phase was extracted with CH2Cl2 (2×10 mL), and the combined organic phases were dried (MgSO4) and concentrated in vacuo. Purification of the crude material by column chromatography on silica gel (150:5:1 CH2Cl2/MeOH/NH4OH) afforded COMPOUND 13 as a colourless foam (47 mg, 69%). 1H NMR (CDCl3) δ 1.62-1.93 (m, 4H), 2.02 (m, 1H), 2.16 (m, 1H), 2.58-2.88 (m, 6H), 3.91 (d, 1H, J=16 Hz), 3.98 (d, 1H, J=16 Hz), 4.02 (m, 1H), 6.86 (s, 2H), 7.18 (m, 3H), 7.43 (d, 1H, J=7.2 Hz), 7.55 (m, 2H), 8.55 (d, 1H, J=3.6 Hz); 13C NMR (CDCl3) δ 21.52, 23.71, 25.96, 26.67, 29.43, 49.21, 51.07, 62.23, 115.28, 120.75, 122.41, 122.81, 135.47, 138.23, 138.86, 146.68, 148.71, 155.28, 157.49. ES-MS m/z 387 (M+H). Anal. Calcd. for C23H26N6.0.21H2O.0.36CH2Cl2: C, 66.67; H, 6.50; N, 19.97. Found: C, 66.77; H, 6.65; N, 19.69.

Workup

  1. concentrationthen concentrated in vacuo
  2. dissolutionThe residue was dissolved in CH2Cl2 (15 mL)
  3. washwashed with 1 N NaOH(aq) (10 mL)
  4. extractionThe aqueous phase was extracted with CH2Cl2 (2×10 mL)
  5. dry with materialthe combined organic phases were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customPurification of the crude material by column chromatography on silica gel (150:5:1 CH2Cl2/MeOH/NH4OH)

Sources & evidence

ORD record
ord-e777a474fe4b446bb4f53c476f8786e3
Source dataset
uspto-grants-2008_04
Patent number
US07354934B2

Reaction notes

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