Hydrochloric Acid → 2-(2-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)acetamido)acetic acid

HRID 216604Notes

Reaction equation

HRID 216604 reaction equation
[OH-].[Li+].[Br:3][C:4]1[N:8]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]#[N:20])=[CH:11][CH:10]=2)[C:7]([S:21][CH2:22][C:23]([NH:25][CH2:26][C:27]([O:29]CC)=[O:28])=[O:24])=[N:6][CH:5]=1.C1COCC1.O.Cl>O>[Br:3][C:4]1[N:8]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([C:19]#[N:20])=[CH:11][CH:10]=2)[C:7]([S:21][CH2:22][C:23]([NH:25][CH2:26][C:27]([OH:29])=[O:28])=[O:24])=[N:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 21881883Oxolane--water (1/1)HCID 59225852HCID 59225852, compound

Product 1

HCID 592258862-(2-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)acetamido)acetic acidYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Aqueous lithium hydroxide solution (1M, 0.47 ml, 0.473 mmol) was added to a solution of ethyl 2-(2-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)acetamido)acetate (112 mg, 0.237 mmol) in 3:1, THF/water (0.95 mL) and stirred for 18 h at room temperature. After concentrating, the crude reaction mixture was acidified with aqueous HCl solution (1M 1.2 mL), diluted with water (10 mL), stirred to break up solids, and filtered to afford 2-(2-(5-bromo-1-(4-cyanonaphthalen-1-yl)-1H-imidazol-2-ylthio)acetamido)acetic acid as an off-white solid (99 mg, 94%).

Workup

  1. concentrationAfter concentrating
  2. customthe crude reaction mixture
  3. stirringstirred
  4. filtrationfiltered

Sources & evidence

ORD record
ord-9846c96cebd04cff83d80fccbf59870f
Source dataset
uspto-grants-2012_06
Patent number
US08193234B2

Reaction notes

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