Tetrahydrofuran → HCID 178437306, compound

HRID 2213689Notes

Reaction equation

HRID 2213689 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[CH:12][C:13]1[N:14]=[CH:15][NH:16][CH:17]=1.C[Si]([N:22]=[C:23]=[O:24])(C)C.O1CCC[CH2:26]1>>[NH:1]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2=[C:12]([C:13]1[N:14]=[CH:15][NH:16][CH:17]=1)[CH3:26])[C:23]([NH2:22])=[O:24]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 70696Trimethylsilyl isocyanateHCID 178507242HCID 178507242, compound

Product 1

HCID 178437306HCID 178437306, compound

Procedure

5-amino-3-[(imidazol-4-yl)methylene]indolin-2-one (0.3 g, 1.3 mmol) was suspended in tetrahydrofuran (100 mL) and trimethylsilylisocyanate (0.5 mL, 3.75 mmol) was added. The reaction mixture was stirred at ambient temperature for three days. The reaction mixture was concentrated and dissolved in acetonitrile/water/TFA. Soluble solids were collected by filtration, dissolved in DMSO and purified with HPLC to afford 80 mg of 5-ureido-3-[1-(imidazol-4-yl)ethylidene]indolin-2-one; as an orange solid, 1H NMR (400 MHz, DMSO-d6) δ 2.6 (s, 3H), 5.8 (s, 2H), 6.8 (d, 1H), 7.3 (m, 1H), 7.9 (s, 1H), 8.3 (s, 1H), 8.5 (s, 1H), 8.9 (s, 1H), 11.1 (s, 1H) ppm.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. dissolutiondissolved in acetonitrile/water/TFA
  3. filtrationSoluble solids were collected by filtration
  4. dissolutiondissolved in DMSO
  5. custompurified with HPLC

Sources & evidence

ORD record
ord-d918457528404cb89567e2dad12867e2
Source dataset
uspto-grants-2006_09
Patent number
US07105563B2

Reaction notes

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