5-Indanyl isocyanate → 2-Amino-4-[4-(3-indan-5-yl-ureido)-phenyl]-thiophene-3-carboxylic acid amide

HRID 349464Notes

Reaction equation

HRID 349464 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].[CH2:17]1[C:25]2[C:20](=[CH:21][C:22]([N:26]=[C:27]=[O:28])=[CH:23][CH:24]=2)[CH2:19][CH2:18]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:27]([NH:26][C:22]3[CH:21]=[C:20]4[C:25](=[CH:24][CH:23]=3)[CH2:17][CH2:18][CH2:19]4)=[O:28])=[CH:12][CH:11]=2)[C:6]=1[C:7]([NH2:9])=[O:8]

Participants

6

Reactant 2

HCID 50036815-Indanyl isocyanateHCID 692588902-Amino4-(4-amino-phenyl)-thiophene-3-carboxylic acid amide

Product 1

HCID 101111262-Amino-4-[4-(3-indan-5-yl-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 5-indanyl 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-indan-5-yl-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-74cca74e2d504ed79bfc7ea3aacce705
Source dataset
uspto-grants-2007_02
Patent number
US07179836B2

Reaction notes

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