2-Aminobenzimidazole → HCID 178517390, compound

HRID 717743Notes

Reaction equation

HRID 717743 reaction equation
C[O:2][C:3](=O)[C:4]([I:8])=[CH:5]OC.[NH:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[NH2:19].C[O-].[Na+]>C(O)C>[I:8][C:4]1[C:3](=[O:2])[N:19]=[C:11]2[NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:10]2[CH:5]=1

Participants

5

Reactant 3

HCID 136242-AminobenzimidazoleHCID 10942334Sodium MethoxideHCID 54067316Methyl 2-iodo-3-methoxyprop-2-enoate

Product 1

HCID 178517390HCID 178517390, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 2-iodo-3-methoxy-acrylic acid methyl ester (1, 1.21 g, 5 mmol), 1H-benzoimidazol-2-ylamine (2, 0.67 g, 5 mmol) and ethanol (30 mL) was added a solution of sodium methoxide (10 mL, 0.5 M in methanol, 5 mmol). The resulted mixture was refluxed for 3 h and concentrated to afford 3-iodo-10H-benzo[4,5]imidazo[1,2-a]pyrimidin-2-one (3). A mixture of (3-tert-butoxycarbonylamino-propyl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]carbamic acid tert-butyl ester (4, 490 mg, 1 mmol), 3 (311 mg, 1 mmol), K2CO2 (414 g, 3 mmol), Pd(PPh3)4 (0) (41 mg, 0.05 mmol), ethanol (6 mL), dioxane (2 mL) and water (2 mL) was degassed and heated at 80° C. for 20 h under argon atmosphere. The reaction mixture was diluted with EtOAc (500 mL), washed with water (300 mL) and brine (300 mL). The organic solution was concentrated and purified by flash chromatography (0%-6% MeOH in methanechloride) to give desired product 5 (170 mg, 31%) as light yellow solid. LCMS (EI) m/z: 570 (M+Na+).

Workup

  1. temperatureThe resulted mixture was refluxed for 3 h
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-762fffeaaf6a40a9969978715fb6985b
Source dataset
uspto-grants-2015_11
Patent number
US09193731B2

Reaction notes

Loading…