Methanol → 3-Ethoxy-3-[3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid ethyl ester

HRID 1747337Notes

Reaction equation

[CH3:1][C:2]1[C:10]2[C:9]([CH2:11][N:12]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=4[NH:14][C:13]3=[O:21])=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH2:22]([O:24][C:25](=[O:31])/[CH:26]=[CH:27]/[O:28][CH2:29][CH3:30])[CH3:23].[OH-].C([N+](C)(C)C)C1C=CC=CC=1.CO.[NH4+].[Cl-]>CN(C=O)C.O>[CH2:22]([O:24][C:25](=[O:31])[CH2:26][CH:27]([O:28][CH2:29][CH3:30])[N:14]1[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N:12]([CH2:11][C:9]2[C:10]3[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][C:6]=3[S:7][CH:8]=2)[C:13]1=[O:21])[CH3:23]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-1,3-dihydro-benzimidazol-2-one (50 mg, 0.17 mmol) in dry DMF (0.7 mL) are added (E)-3-Ethoxy-acrylic acid ethyl ester (0.049 mL, 0.34 mmol) and 40% benzyltrimethyl ammonium hydroxide in MeOH (0.008 mL, 0.017 mmol). The resulting mixture is warmed up to 60° C. for 16 hr and then saturated NH4Cl solution (1 mL) is added followed by water (5 mL). The mixture is extracted with EtOAc (3×10 mL). The organic layers are combined, dried and concentrated to give crude product. Purification by flash column chromatography using EtOAc in hexane (from 0% to 30%) affords 50 mg (67%) of 3-Ethoxy-3-[3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid ethyl ester.

Workup

extractionThe mixture is extracted with EtOAc (3×10 mL)
customdried
concentrationconcentrated
customto give crude product
customPurification by flash column chromatography

Sources & evidence

ORD record: ord-d61625fd61e64348a32a495bcf0c4012
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150556B2

Reaction notes

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