Aniline → HCID 137629483, compound

HRID 229452Notes

Reaction equation

HRID 229452 reaction equation
[Br:1][C:2]1[S:6][C:5]([NH:7][C:8](=[O:17])[CH2:9][CH:10]2[S:14][C:13](=[NH:15])[NH:12][C:11]2=[O:16])=[C:4]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:3]=1[CH2:23]Br.[NH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>>[NH:25]([CH2:23][C:3]1[C:4]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:5]([NH:7][C:8](=[O:17])[CH2:9][CH:10]2[S:14][C:13](=[NH:15])[NH:12][C:11]2=[O:16])[S:6][C:2]=1[Br:1])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 6115AnilineHCID 140511257HCID 140511257, compound

Product 1

HCID 137629483HCID 137629483, compoundYield 20%

Procedure

To ethyl 5-bromo-4-(bromomethyl)-2-{[(2-imino-4-oxo-1,3-thiazolidin-5-yl) acetyl]amino}thiophene-3-carboxylate (25 mg, 0.05 mmol) in N,N dimethyl formaide (1 mL) was added aniline (10 mg, 0.11 mmol). The reaction mixture was stirred at room temperature for 16 h. Then the reaction mixture was concentrated and purified by reverse phase column to yield ethyl 4-(anilinomethyl)-5-bromo-2-{[(2-imino-4-oxo-1,3-thiazolidin-5-yl)acetyl]amino}thiophene-3-carboxylate (5.0 mg, 20% yield).

Workup

  1. concentrationThen the reaction mixture was concentrated
  2. custompurified by reverse phase column

Sources & evidence

ORD record
ord-2d659069f990454aad4d7e65f23349e7
Source dataset
uspto-grants-2009_07
Patent number
US07563813B2

Reaction notes

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