Hydrochloric Acid → 5-[2-[(4-Chlorophenyl)amino]-1-(4-methylpiperazin-1-yl)-2-oxoethyl]thiophene-2-carboxylic acid

HRID 1919886Notes

Reaction equation

HRID 1919886 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:28])[CH:10]([C:18]2[S:22][C:21]([C:23]([O:25]CC)=[O:24])=[CH:20][CH:19]=2)[N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1.[Li+].[OH-].Cl>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:28])[CH:10]([C:18]2[S:22][C:21]([C:23]([OH:25])=[O:24])=[CH:20][CH:19]=2)[N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 57611900Ethyl 5-[2-[(4-chlorophenyl)amino]-1-(4-methylpiperazin-1-yl)-2-oxoethyl]thiophene-2-carboxylate

Product 1

HCID 576119375-[2-[(4-Chlorophenyl)amino]-1-(4-methylpiperazin-1-yl)-2-oxoethyl]thiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Ethyl 5-[2-[(4-chlorophenyl)amino]-1-(4-methylpiperazin-1-yl)-2-oxoethyl]thiophene-2-carboxylate (0.56 g, 1.33 mmol) was made 0.5 M in dioxane and to this stirring solution was added 3 equivalents 3M LiOH (1.33 mL, 3.98 mmol). The resulting mixture was stirred at ambient temperature for 3 hours. The mixture was adjusted to pH 6 with 1 M HCl then concentrated in vacuo to give the desired product. MS: cal'd 394, 396 (MH+), exp 394, 396 (MH+).

Workup

  1. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-bbcb9ad0e8cc4d37b4b35ae5973a90db
Source dataset
uspto-grants-2012_05
Patent number
US08168658B2

Reaction notes

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