Hydrochloric Acid → HCID 59497244, compound

HRID 1747282Notes

Reaction equation

HRID 1747282 reaction equation
C([O:3][C:4](=[O:28])[CH2:5][CH2:6][N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([CH2:16][C:17]2[C:18]3[CH:25]=[C:24]([Cl:26])[CH:23]=[CH:22][C:19]=3[S:20][CH:21]=2)[C:8]1=[O:27])C.[OH-].[Na+].Cl>CO>[Cl:26][C:24]1[CH:23]=[CH:22][C:19]2[S:20][CH:21]=[C:17]([CH2:16][N:9]3[C:10]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[N:7]([CH2:6][CH2:5][C:4]([OH:28])=[O:3])[C:8]3=[O:27])[C:18]=2[CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59497627HCID 59497627, compound

Product 1

HCID 59497244HCID 59497244, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-[3-(5-Chloro-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid ethyl ester (50 mg, 0.12 mmol) in MeOH (3 mL) was added 2N NaOH (1 mL). The reaction mixture was stirred at room temperature for 1 h. The solution was then treated with 1M HCl solution until pH ˜4 and extracted with CH2Cl2. The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 95:5 CH2Cl2:MeOH as an eluent to afford 20 mg (42%) of the desired product as a white solid. LCMS (ESMS): m/z 387.89 (M+H+).

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-3738031d4fdd429dbf2699bb96c4bad6
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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