Phenyl isocyanate → 2-Amino4-{4-[3-phenyl-ureido]-phenyl}-thiophene-3-carboxylic acid amide

HRID 349463Notes

Reaction equation

HRID 349463 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:10]2[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=2)[C:6]=1[C:7]([NH2:9])=[O:8].[C:17]1([N:23]=[C:24]=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1.CO.C(N(CC)CC)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:24]([NH:23][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:25])=[CH:12][CH:11]=2)[C:6]=1[C:7]([NH2:9])=[O:8]

Participants

6

Reactant 2

HCID 7672Phenyl isocyanateHCID 692588902-Amino4-(4-amino-phenyl)-thiophene-3-carboxylic acid amide

Product 1

HCID 101326942-Amino4-{4-[3-phenyl-ureido]-phenyl}-thiophene-3-carboxylic acid amide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

Crude 2-amino-4-(4-amino-phenyl)-thiophene-3-carboxylic acid amide (0.15 mmoles, 1 eq) is dissolved in 5 mL THF and treated with 400 μL of 0.35 M THF solution of phenyl isocyanate (0.15 mmoles, 1 eq). When the reaction is complete, as judged by TLC analysis, the reaction mixture is diluted with 1 mL methanol and 1 mL triethylamine, stirred for 30 minutes, and concentrated to dryness. The residue is purified by prep HPLC yielding pure 2-amino-4-{4-[3-phenyl-ureido]-phenyl}-thiophene-3-carboxylic acid amide.

Workup

  1. concentrationconcentrated to dryness
  2. customThe residue is purified by prep HPLC

Sources & evidence

ORD record
ord-be61e41b723141ec82628f0c102c81a9
Source dataset
uspto-grants-2007_02
Patent number
US07179836B2

Reaction notes

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