Potassium Carbonate → 5-(5-Chlorobenzoxazol-2-yl)-2-(3-methoxycarbonylphenyl)-1-(tetrahydropyran-4-yl)benzimidazole

HRID 74286Notes

Reaction equation

HRID 74286 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][C:13]([NH:17][CH:18]4[CH2:23][CH2:22][O:21][CH2:20][CH2:19]4)=[C:14]([CH:16]=3)[NH2:15])=[N:7][C:6]=2[CH:24]=1.[CH:25]([C:27]1[CH:28]=[C:29]([CH:34]=[CH:35][CH:36]=1)[C:30]([O:32][CH3:33])=[O:31])=O.OOS([O-])=O.[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:11]=[CH:12][C:13]4[N:17]([CH:18]5[CH2:19][CH2:20][O:21][CH2:22][CH2:23]5)[C:25]([C:27]5[CH:36]=[CH:35][CH:34]=[C:29]([C:30]([O:32][CH3:33])=[O:31])[CH:28]=5)=[N:15][C:14]=4[CH:16]=3)=[N:7][C:6]=2[CH:24]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 639145Methyl 3-formylbenzoateHCID 23707502Potassium hydroxy sulfiteHCID 674984215-Chloro-2-(2-(tetrahydropyran-4-yl)aminoanilin-5-yl)benzoxazole

Product 1

HCID 674981815-(5-Chlorobenzoxazol-2-yl)-2-(3-methoxycarbonylphenyl)-1-(tetrahydropyran-4-yl)benzimidazoleYield 62%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 5-chloro-2-(2-(tetrahydropyran-4-yl)aminoanilin-5-yl)benzoxazole (see Working Example 100-2) (250 mg, 0.727 mmol) in dimethylformamide (3 mL) was added methyl 3-formylbenzoate (143 mg, 0.872 mmol) and oxone (313 mg, 0.509 mmol), and this was stirred at room temperature for 2 hours. After the reaction was complete, aqueous potassium carbonate solution was added, this was filtered and washed with water. The crystals obtained were purified by silica gel column chromatography to yield the title compound (220 mg, 62% yield) as yellow crystals.

Workup

  1. filtrationthis was filtered
  2. washwashed with water
  3. customThe crystals obtained
  4. customwere purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6b3da85a93b445ed99b6e7eccece207d
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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