Hydrochloric Acid → HCID 59497401, compound

HRID 1747420Notes

Reaction equation

HRID 1747420 reaction equation
C[O:2][C:3](=[O:31])[CH2:4][CH:5]([N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([CH2:18][C:19]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][C:26]=3[CH3:28])[N:21]([CH3:29])[CH:20]=2)[C:10]1=[O:30])[CH2:6][O:7][CH3:8].Cl>O1CCOCC1.O>[CH3:29][N:21]1[C:22]2[C:27](=[C:26]([CH3:28])[CH:25]=[CH:24][CH:23]=2)[C:19]([CH2:18][N:11]2[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N:9]([CH:5]([CH2:6][O:7][CH3:8])[CH2:4][C:3]([OH:31])=[O:2])[C:10]2=[O:30])=[CH:20]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 59497465HCID 59497465, compound

Product 1

HCID 59497401HCID 59497401, compoundYield 12.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 3-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-4-methoxy-butyric acid methyl ester (200 mg, 0.48 mmol) in 1,4-dioxane (2.0 mL) is added LiOH monohydrate (25 mg, 0.59 mmol) in water (2.0 mL) at room temperature. The solution is stirred at the same temperature for 2 hours. Then 1.0 mL of 1.0 M HCl solution is added along with 10 mL of water. Then the mixture is extracted with EtOAc (3×25 mL) and the organic layers are combined, dried and concentrated to give 190 mg (97%) of crude product. 30 mg of this crude is purified by preparative TLC to give 25 mg of 3-[3-(1,4-Dimethyl-1H-indol-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-4-methoxy-butyric acid. LCMS (ESMS): m/z 408.25 (M+H+).

Workup

  1. extractionThen the mixture is extracted with EtOAc (3×25 mL)
  2. customdried
  3. concentrationconcentrated
  4. customto give 190 mg (97%) of crude product
  5. custom30 mg of this crude is purified by preparative TLC

Sources & evidence

ORD record
ord-e8791ed8bc6d4013ab8354d11511f86e
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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