Urea → methyl 6-(4-morpholinyl)-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylate

HRID 44543

Reaction equation

HRID 44543 reaction equation
[NH2:1][C:2]1[C:11]([NH2:12])=[CH:10][C:9]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].N[C:20](N)=[O:21]>CN(C=O)C.C(Cl)Cl>[N:13]1([C:9]2[CH:8]=[C:3]([C:4]([O:6][CH3:7])=[O:5])[C:2]3[NH:1][C:20](=[O:21])[NH:12][C:11]=3[CH:10]=2)[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1

Participants

5

Reactant 2

HCID 1176UreaHCID 58279190Methyl 2,3-diamino-5-morpholinobenzoate

Product 1

HCID 66976929methyl 6-(4-morpholinyl)-2-oxo-2,3-dihydro-1H-benzimidazole-4-carboxylateYield 62%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
170 °C

Procedure

To a solution of methyl 2,3-diamino-5-(4-morpholinyl)benzoate, prepared as described in Example 45, step a (11.0 g, 4.0 mmol) in DMF (50 mL) was added urea (720 mg, 12 mmol) and the mixture was heated to 170° C. for 4 h. When analysis by TLC showed no starting material remaining, the mixture was cooled to room temperature then diluted with DCM (200 mL), washed with water (50 mL×2) and dried over anhydrous Na2SO4, filtered and concentrated in-vacuo. The residue was then purified by chromatography on silica (eluted with EtOAc) to afford the desired product as a dark-yellow solid (690 mg, 62%).

Workup

  1. temperaturethe mixture was cooled to room temperature
  2. washwashed with water (50 mL×2)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in-vacuo
  6. customThe residue was then purified by chromatography on silica (eluted with EtOAc)

Sources & evidence

ORD record
ord-ad3ac8be07ae4b6ca8683d71599c1acd
Source dataset
uspto-grants-2013_09
Patent number
US08541411B2

Linked notes

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