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Lithium hydroxide, monohydrate → 3-{3-[(4-chloro-1,2,3-trimethyl-1H-indol-7-yl)methyl]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}hexanoic acid

HRID 1747361
Notes
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Reaction equation

HRID 1747361 reaction equation
C([O:3][C:4](=[O:34])[CH2:5][CH:6]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH2:19][C:20]2[CH:21]=[CH:22][C:23]([Cl:32])=[C:24]3[C:28]=2[N:27]([CH3:29])[C:26]([CH3:30])=[C:25]3[CH3:31])[C:11]1=[O:33])[CH2:7][CH2:8][CH3:9])C.O.[OH-].[Li+]>C1COCC1.O>[Cl:32][C:23]1[CH:22]=[CH:21][C:20]([CH2:19][N:12]2[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:10]([CH:6]([CH2:7][CH2:8][CH3:9])[CH2:5][C:4]([OH:34])=[O:3])[C:11]2=[O:33])=[C:28]2[C:24]=1[C:25]([CH3:31])=[C:26]([CH3:30])[N:27]2[CH3:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 59497398HCID 59497398, compound

Product 1

HCID 594973483-{3-[(4-chloro-1,2,3-trimethyl-1H-indol-7-yl)methyl]-2-oxo-2,3-dihydro-1H-benzimidazol-1-yl}hexanoic acidYield 44.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028Tetrahydrofuran
Solvent

Procedure

To a stirred solution of 3-[3-(4-Chloro-1,2,3-trimethyl-1H-indol-7-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl ester (25 mg, 0.05 mmol) in THF (5 ml) and water (1 ml) was added lithium hydroxide monohydrate (20 mg, 0.48 mmol). The resulting mixture was stirred at ambient temperature until all of the starting material was consumed. After this time the reaction was concentrated to low volume and diluted with water (5 ml) and acetic acid (0.2 ml). The resulting solid was collected via filtration and suspended in acetonitrile/water. The solid was collected once more via filtration and dried on house vacuum at 70° C. to give 10 mg (43%) of the desired product. LCMS (ESMS): m/z 454.96 (M+H+).

Workup

  1. customwas consumed
  2. concentrationAfter this time the reaction was concentrated to low volume
  3. additiondiluted with water (5 ml) and acetic acid (0.2 ml)
  4. filtrationThe resulting solid was collected via filtration
  5. filtrationThe solid was collected once more via filtration
  6. customdried on house vacuum at 70° C.

Sources & evidence

ORD record
ord-9a47061abf2b4159a59ff34dac7e2493
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09150556B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes