Water → HCID 21876117, compound

HRID 1454659Notes

Reaction equation

HRID 1454659 reaction equation
[Cl:1][C:2]1[C:3]([NH2:22])=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][CH3:11])[N:7]([C:12]3[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][Cl:20])=[CH:14][CH:13]=3)[C:6]=2[CH:21]=1.[C:23](Cl)(=[O:25])[CH3:24].O>N1C=CC=CC=1>[Cl:1][C:2]1[C:3]([NH:22][C:23](=[O:25])[CH3:24])=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][CH3:11])[N:7]([C:12]3[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][Cl:20])=[CH:16][CH:17]=3)[C:6]=2[CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 67098663HCID 67098663, compound

Product 1

HCID 21876117HCID 21876117, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 6-chloro-1-[4-(2-chloroethyl)phenyl]-2-ethyl-1H-benzimidazol-5-ylamine (step 6 of Example 110, 100 mg, 0.3 mmol) in pyridine (7 mL) was added dropwise acetyl chloride (0.03 mL, 0.33 mmol) under nitrogen atmosphere at 0° C., and the reaction mixture was stirred at room temperature for 1.5 h. The mixture was poured into water (20 mL) and extracted with ethyl acetate (50 mL). The organic layer was washed with 2N aqueous NaOH (30 mL), brine (30 mL), then dried (Na2SO4). After removal of solvent, the crude product was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (1:3) to afford 110 mg (98%) of the title compound as white solids: 1H-NMR (CDCl3) δ: 8.66 (1H, s), 7.56 (1H, br.s), 7.45 (2H, d, J=8.2 Hz), 7.29 (2H, d, J=8.2 Hz), 7.12 (1H, s), 3.82 (2H, t, J=7.1 Hz), 3.19 (2H, t, J=7.1 Hz), 2.77 (2H, q, J=7.6 Hz), 2.26 (3H, s), 1.34 (3H, t, J=7.6 Hz).

Workup

  1. extractionextracted with ethyl acetate (50 mL)
  2. washThe organic layer was washed with 2N aqueous NaOH (30 mL), brine (30 mL)
  3. dry with materialdried (Na2SO4)
  4. customAfter removal of solvent
  5. customthe crude product was purified by flash column chromatography on silica gel eluting with hexane/ethyl acetate (1:3)

Sources & evidence

ORD record
ord-4a6333d3551e45998c1b0ceacff20afe
Source dataset
uspto-grants-2009_01
Patent number
US07479564B2

Reaction notes

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