Hydrochloric Acid → HCID 59497528, compound

HRID 1747461Notes

Reaction equation

HRID 1747461 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[CH:27]=[C:26]([Br:28])[CH:25]=[C:24]3[C:20]=2[CH2:21][C:22](=[O:29])[NH:23]3)[C:10]1=[O:30])[CH2:6][CH2:7][CH3:8].[OH-].[Li+].Cl>O1CCOCC1.O>[Br:28][C:26]1[CH:25]=[C:24]2[C:20]([CH2:21][C:22](=[O:29])[NH: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][CH2:7][CH3:8])[CH2:4][C:3]([OH:31])=[O:2])[C:10]2=[O:30])[CH:27]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 67360730Methyl 3-[(6-bromo-2,3-dihydro-2-oxo-1H-indol-4-yl)methyl]-2,3-dihydro-2-oxo-β-propyl-1H-benzimidazole-1-propanoate

Product 1

HCID 59497528HCID 59497528, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

3-[3-(6-Bromo-2-oxo-2,3-dihydro-1H-indol-4-ylmethyl)-2-oxo-2,3-dihydro-benzoimidazol-1-yl]-hexanoic acid methyl ester 80 mg (0.16 mmol) is dissolved in 2.5 mL of dioxane and then lithium hydroxide (10 mg, 0.43 mmol in 1.5 mL of water) is added drop wise to the reaction mixture. The reaction is stirred at room temperature and monitored by LC/MS. Upon completion the reaction is acidified by the addition of 1N HCl, and diluted with 10 mL of water. A solid precipitated that is collected and dried to give the title compound (73 mg. 0.15 mmol 96%). LCMS (ESMS): m/z 473.1 (M+H+).

Workup

  1. customA solid precipitated that
  2. customis collected
  3. customdried

Sources & evidence

ORD record
ord-dbbfefb2bc374d0d898f9a2ac88d20e4
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

Loading…