Dimethylformamide → HCID 67011796, compound

HRID 2111782Notes

Reaction equation

HRID 2111782 reaction equation
Cl[CH:2]([CH3:30])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]3[CH:16]=[CH:17][C:18]([C:20]([NH:22][CH2:23][C:24]4[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=4)=[O:21])=[CH:19][C:14]=3[N:13]=[CH:12]2)=[CH:7][CH:6]=1.[F:31][C:32]([F:42])([F:41])[O:33][C:34]1[CH:35]=[C:36]([OH:40])[CH:37]=[CH:38][CH:39]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>C(#N)C.O>[N:26]1[CH:27]=[CH:28][CH:29]=[C:24]([CH2:23][NH:22][C:20]([C:18]2[CH:17]=[CH:16][C:15]3[N:11]([C:8]4[CH:9]=[CH:10][C:5]([O:4][CH2:3][CH2:2][CH2:30][O:40][C:36]5[CH:37]=[CH:38][CH:39]=[C:34]([O:33][C:32]([F:31])([F:41])[F:42])[CH:35]=5)=[CH:6][CH:7]=4)[CH:12]=[N:13][C:14]=3[CH:19]=2)=[O:21])[CH:25]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27332613-(Trifluoromethoxy)phenolHCID 69069026HCID 69069026, compound

Product 1

HCID 67011796HCID 67011796, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

1-[4-(2-Chloropropoxy)phenyl]-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide (prepared as described above using 1-(4-hydroxyphenyl)-N-pyridin-3-ylmethyl-1H-benzimidazole-5-carboxamide as phenol and 1-bromo-3-chloropropane as alkylating agent) (100 mg, 0.24 mmol), 3-trifluoromethoxyphenol (42 mg, 31 μL 0.24 mmol) and potassium carbonate (36 mg, 0.26 mmol) were suspended in acetonitrile (2 mL), DMF (1 mL), and water (0.5 mL) and the mixture stirred at 60° C. for 18 h. The reaction mixture was then concentrated in vacuo and purified by reverse-phase preparative HPLC to give N-pyridin-3-ylmethyl-1-(4-{3-[3-(trifluoromethoxy) phenoxy]propoxy}phenyl)-1H-benzimidazole-5-carboxamide. 1H NMR (CDCl3, 400 MHz): δ 8.66 (d, J=2.0 Hz, 1H), 8.56 (dd, J=4.8, 1.2 Hz, 1H), 8.34 (d, J=1.6 Hz, 1H), 8.05 (s, 1H), 7.90 (dd, J=8.4, 1.6 Hz, 1H), 7.78 (ddd, J=8.0, 2.0, 2.0 Hz, 1H), 7.48 (d, J=8.0 Hz, 1H), 7.43-7.37 (m, 2H), 7.34-7.28 (m, 2H), 7.20-7.08 (m, 3H), 6.90-6.78 (m, 3H), 4.75 (d, J=5.6 Hz, 2H), 4.27 (t, J=6.0 Hz, 2H), 4.22 (t, J=6.0 Hz, 2H), 2.35 (quin, J=6.0 Hz, 2H); MS (ES+): m/z 563 [MH+]

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. custompurified by reverse-phase preparative HPLC

Sources & evidence

ORD record
ord-a7620adad3b34ea0ad2ce6d7f0559c92
Source dataset
uspto-grants-2009_04
Patent number
US07521448B2

Reaction notes

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