Hydrochloric Acid → HCID 69545260, compound

HRID 2213686Notes

Reaction equation

HRID 2213686 reaction equation
C(OC(C[NH:7][C:8](=[O:27])[NH:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14](=[O:19])[C:13]2=[C:20]([C:22]1[NH:23][CH:24]=[CH:25][CH:26]=1)[CH3:21])=O)C.[H-].[Na+].[C:30](OCC)(=[O:32])[CH3:31].Cl>O1CCCC1.O>[O:27]=[C:8]1[NH:7][C:30](=[O:32])[CH2:31][N:9]1[C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14](=[O:19])[C:13]2=[C:20]([C:22]1[NH:23][CH:24]=[CH:25][CH:26]=1)[CH3:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 69589137HCID 69589137, compound

Product 1

HCID 69545260HCID 69545260, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-(N′-(ethoxycarbonylmethyl)ureido)-3-[1-(pyrrol-2-yl)ethylidene]indolin-2-one (95 mg, 0.25 mmol) in tetrahydrofuran (2.5 mL) was treated with NaH (16 mg, 0.40 mmol). After stirring overnight, ethyl acetate (15 mL) and water (5 mL) were added and the reaction mixture was neutralized with 6N HCl. The organic layer dried (NaSO4) and concentrated to afford a crude product (90 mg). Purification by reverse phase HPLC (acetonitrile/water) afforded 5-(2,4-dioxoimidazolidin-1-yl)-3-[1-(pyrrol-2-yl)ethylidene]indolin-2-one; (8 mg); 1H NMR (400 MHz, DMSO-d6) δ 2.72 (s, 3H), 4.02 (s, 2H), 6.36 (m, 1H), 6.96 (d, 1H), 7.04 (m, 2H), 7.36 (d, 1H), 7.60 (m, 1H), 8.22 (s, 1H), 11.14 (s, 1H) ppm.

Workup

  1. dry with materialThe organic layer dried (NaSO4)
  2. concentrationconcentrated
  3. customto afford a crude product (90 mg)
  4. customPurification by reverse phase HPLC (acetonitrile/water)

Sources & evidence

ORD record
ord-7b2eedf44fcb4d4ba6236c7edbdce24b
Source dataset
uspto-grants-2006_09
Patent number
US07105563B2

Reaction notes

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