Dimethylformamide → HCID 9815072, compound

HRID 898718Notes

Reaction equation

HRID 898718 reaction equation
Cl[CH2:2][C:3]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[N:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:18][N:19]([CH3:22])[CH:20]=O>C(OCC)(=O)C>[CH3:8][C@H:6]1[CH2:20][N:19]([C:22]2[CH:9]=[CH:10][CH:11]=[CH:5][N:4]=2)[CH2:18][CH2:3][N:7]1[CH2:2][C:3]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[N:4]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 785712-Chloromethylbenzimidazole

Product 1

HCID 9815072HCID 9815072, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 25B (0.24 g, 1.33 mmol) in N,N-dimethylformamide (10 mL) was treated with 2-chloromethyl-1H-benzimidazole (0.21 g, 1.27 mmol) and cesium carbonate (0.41 mmol, 1.27 mmol) at 23° C. with stirring for 3 hours. The reaction mixture was diluted with ethyl acetate and washed with water (3×) and brine, dried over Na2SO4 filtered, and the filtrate concentrated under reduced pressure. The residue was chromatographed on flash silica gel (1-3% methanol/dichloromethane gradient) to afford 178 mg (46% yield) of the title compound as a light yellow solid. mp 149-151° C.; 1H NMR (400 MHz, DMSO-d6) δ 1.18 (d, J=6 Hz, 3H), 2.38 (m, 1H), 2.53 (m, 1H), 2.76 (dd, J=8, 11.2 Hz, 1H), 2.83 (m, 1H), 3.03 (m, 1H), 3.69 (d, J=14 Hz, 1H), 3.94 (m, 1H), 4.00 (m, 1H), 4.07 (d, J=14 Hz, 1H), 6.60 (dd, J=4.8, 6.4 Hz, 1H), 6.80 (d, J=8.4 Hz, 1H), 7.13 (m, 2H), 7.60 (m, 3H), 8.08 (m, 1H), 12.22 (bs, 1H); MS (ESI) m/e 308 (M+H)+; Anal. calcd for C18H21N5: C, 70.33; H, 6.89; N, 22.78. Found: C, 70.21; H, 6.77; N, 22.62.

Workup

  1. washwashed with water (3×) and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under reduced pressure
  5. customThe residue was chromatographed on flash silica gel (1-3% methanol/dichloromethane gradient)

Sources & evidence

ORD record
ord-267d8e1063b24106a377213bd5a332a9
Source dataset
uspto-grants-2008_04
Patent number
US07351828B2

Reaction notes

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