Triethylamine → {2-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-ethylamino}-acetic acid methyl ester

HRID 1747431Notes

Reaction equation

HRID 1747431 reaction equation
Br[CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:13][C:14]2[C:15]3[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:16]=3[S:17][CH:18]=2)[C:5]1=[O:24].[Cl-].[CH3:26][O:27][C:28]([CH2:30][NH3+:31])=[O:29].CCN(CC)CC.C([O-])([O-])=O.[Na+].[Na+]>CC#N.O>[CH3:26][O:27][C:28](=[O:29])[CH2:30][NH:31][CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]([CH2:13][C:14]2[C:15]3[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][C:16]=3[S:17][CH:18]=2)[C:5]1=[O:24]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 10340Sodium Carbonate2×HCID 11105367(Methoxycarbonylmethyl)ammonium chloride2×HCID 594972451-(2-Bromo-ethyl)-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one

Product 1

HCID 67358337{2-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-ethylamino}-acetic acid methyl esterYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

1-(2-Bromo-ethyl)-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one (30 mg, 0.075 mmol) is dissolved in CH3CN (0.5 mL)) and Methoxycarbonylmethyl-ammonium chloride (11 mg, 0.09 mmol) and Et3N (0.025 mL, 0.18 mmol) are added. The mixture is first stirred at room temperature for 16 hr. And then 11 mg of Na2CO3 is added and the mixture is stirred at room temperature for another 48 hr. Since the reaction is not completed, another 11 mg of Methoxycarbonylmethyl-ammonium chloride, 0.025 mL of Et3N and 11 mg of Na2CO3 are added. The mixture is then heated at 80° C. for 20 hrs. Then 10 mL of water is added and the mixture is extracted with EtOAc (3×15 mL). The organic layers are combined, dried and concentrated to give crude product. Purification by flash column chromatography affords 30 mg (98%) of {2-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-ethylamino}-acetic acid methyl ester.

Workup

  1. additionare added
  2. stirringthe mixture is stirred at room temperature for another 48 hr
  3. temperatureThe mixture is then heated at 80° C. for 20 hrs
  4. extractionthe mixture is extracted with EtOAc (3×15 mL)
  5. customdried
  6. concentrationconcentrated
  7. customto give crude product
  8. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-208d8bdf998b4705b45254abc2e752a4
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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