Trifluoroacetic acid → HCID 67011225, compound

HRID 2111795Notes

Reaction equation

HRID 2111795 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([C:17]([NH:19][CH2:20][C:21]4[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=4)=[O:18])=[CH:16][C:11]=3[N:10]=[CH:9]2)[CH:5]=[CH:6][CH:7]=1.[CH:27](=O)[C:28]1[CH:33]=[CH:32][CH:31]=[N:30][CH:29]=1.C(O)(C(F)(F)F)=O.[SiH](CC)(CC)CC>C(Cl)Cl>[N:30]1[CH:31]=[CH:32][CH:33]=[C:28]([CH2:27][NH:1][C:2]2[CH:3]=[C:4]([N:8]3[C:12]4[CH:13]=[CH:14][C:15]([C:17]([NH:19][CH2:20][C:21]5[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=5)=[O:18])=[CH:16][C:11]=4[N:10]=[CH:9]3)[CH:5]=[CH:6][CH:7]=2)[CH:29]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 103713-PyridinecarboxaldehydeHCID 12052TriethylsilaneHCID 69067477HCID 69067477, compound

Product 1

HCID 67011225HCID 67011225, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(3-aminophenyl)-N-(pyridin-3-ylmethyl)-1H-benzimidazole-5-carboxamide (prepared in Steps (a)-(d) of the procedure used for the synthesis of EXAMPLE I1, 70.2 mg, 0.205 mmol) and nicotinaldehyde (20 μL, 0.21 mmol) in DCM (1 mL) under N2 was treated with TFA (1 mL) and after 5 min was heated at reflux for 2 h. The cooled reaction mixture was then treated with Et3SiH (70 μL, 0.44 mmol) and the mixture re-heated to reflux for 19 h. After this time the solvents and excess reagents were removed by concentration in vacuo and the crude residue purified by column chromatography over silica gel eluting with 0.7-15% MeOH/DCM to provide the title compound; MS (ES+): m/z 435 [MH+]

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. customThe cooled reaction mixture
  4. temperaturethe mixture re-heated
  5. temperatureto reflux for 19 h
  6. customAfter this time the solvents and excess reagents were removed by concentration in vacuo
  7. customthe crude residue purified by column chromatography over silica gel eluting with 0.7-15% MeOH/DCM

Sources & evidence

ORD record
ord-b7a5c43647ca4006aee1ec07ecbffe39
Source dataset
uspto-grants-2009_04
Patent number
US07521448B2

Reaction notes

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