Trifluoroacetic acid → HCID 178423615, compound

HRID 2174073Notes

Reaction equation

HRID 2174073 reaction equation
[CH3:1][C:2]1[C:3]([CH2:12][C:13]2[NH:17][C:16]3[CH:18]=[CH:19][C:20]([C:22]#[N:23])=[CH:21][C:15]=3[N:14]=2)=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[NH:7][CH:6]=[CH:5]2.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][C:2]1[C:3]([CH2:12][C:13]2[NH:17][C:16]3[CH:18]=[CH:19][C:20]([C:22]#[N:23])=[CH:21][C:15]=3[N:14]=2)=[C:4]2[C:8](=[C:9]([CH3:11])[CH:10]=1)[NH:7][CH2:6][CH2:5]2

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 178424030HCID 178424030, compound

Product 1

HCID 178423615HCID 178423615, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-((5,7-Dimethyl-1H-indol-4-yl)methyl)-1H-benzo[d]imidazole-5-carbonitrile (35 mg, 0.117 mmol) was suspended in DCM (1 mL), triethylsilane (0.37 mL, 2.33 mmol) and then TFA (0.5 mL) were added and the reaction was stirred at room temperature. After 1 hour the reaction was concentrated and then the resulting residue was dissolved in EtOAc and treated with 1 mL of aq. ammonium hydroxide. The residue was purified via FCC (0-100% EtOAc in heptanes) to obtain the title compound. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.47 (d, J=15.66 Hz, 1H) 8.02 (m) 7.88 (m) 7.56 (m) 7.50-7.54 (m) 6.60 (s, 1H) 5.08 (br. s., 1H) 4.08 (d, J=3.54 Hz, 2H) 3.40 (t, J=8.46 Hz, 2H) 2.91 (t, J=8.46 Hz, 2H) 2.09 (s, 3H) 1.94-2.03 (m, 3H). HRMS calcd. for C19H18N4 (M+H)+, 303.1604. found 303.1615.

Workup

  1. concentrationAfter 1 hour the reaction was concentrated
  2. dissolutionthe resulting residue was dissolved in EtOAc
  3. additiontreated with 1 mL of aq. ammonium hydroxide
  4. customThe residue was purified via FCC (0-100% EtOAc in heptanes)

Sources & evidence

ORD record
ord-15bbf96c27514ca18eb05b0ca870a7eb
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

Loading…