Methanol → 5-(Benzoxazol-2-yl)-2-methyl-1-(3-(morpholin-4-yl)-n-propyl)benzimidazole

HRID 74280Notes

Reaction equation

HRID 74280 reaction equation
N1([CH:7]([CH3:28])[CH2:8][NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]3[O:17][C:18]4[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=4[N:20]=3)=[CH:12][C:11]=2[N+:25]([O-])=O)CCOCC1.Cl.[C:30](=[NH:34])(OC)[CH3:31].[C:35](=[O:38])([O-])O.[Na+].[CH2:40](OCC)[CH3:41].[CH3:45]O>>[O:17]1[C:18]2[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=2[N:20]=[C:16]1[C:13]1[CH:14]=[CH:15][C:10]2[N:9]([CH2:8][CH2:7][CH2:28][N:34]3[CH2:45][CH2:35][O:38][CH2:31][CH2:30]3)[C:40]([CH3:41])=[N:25][C:11]=2[CH:12]=1

Participants

6

Reactant 5

HCID 887MethanolHCID 3283Diethyl EtherHCID 516892Sodium BicarbonateHCID 10313100Ethanimidic acid, methyl ester, hydrochloride (1:1)HCID 674985632-(N-(2-(morpholin-4-yl)-n-propyl)-2-nitroanilin-4-yl)benzoxazole

Product 1

HCID 674984495-(Benzoxazol-2-yl)-2-methyl-1-(3-(morpholin-4-yl)-n-propyl)benzimidazoleYield 61%

Procedure

To a solution of 2-(2-(3-(morpholin-4-yl)-n-propyl)aminoanilin-4-yl)benzoxazole (see Working Example 96-1) (300 mg, 0.851 mmol) in methanol (5 mL) was added methyl acetimidate hydrochloride (103 mg, 0.936 mmol), and this was heated to reflux for 3 hours. After the reaction was complete, saturated aqueous sodium hydrogen carbonate solution was added, and this was extracted with ethyl acetate. After the organic layer obtained was dried over anhydrous sodium sulfate, it was filtered and concentrated. To the crystals obtained was added diethyl ether, this was filtered, washed with diethyl ether, and dried to yield the title compound (195 mg, 61% yield) as light brown crystals.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux for 3 hours
  3. extractionthis was extracted with ethyl acetate
  4. customAfter the organic layer obtained
  5. dry with materialwas dried over anhydrous sodium sulfate, it
  6. filtrationwas filtered
  7. concentrationconcentrated
  8. customTo the crystals obtained
  9. filtrationthis was filtered
  10. washwashed with diethyl ether
  11. customdried

Sources & evidence

ORD record
ord-e4c8259744514d4c816fc342c2a97742
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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