Methanol → HCID 69589137, compound

HRID 2213685Notes

Reaction equation

HRID 2213685 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=[C:12]([C:14]1[NH:15][CH:16]=[CH:17][CH:18]=1)[CH3:13].[N:19]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:20]=[O:21].CO>O1CCCC1>[CH2:26]([O:25][C:23]([CH2:22][NH:19][C:20](=[O:21])[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:14]1[NH:15][CH:16]=[CH:17][CH:18]=1)[CH3:13])=[O:24])[CH3:27]

Participants

5

Reactant 3

HCID 887MethanolHCID 76283Ethyl isocyanatoacetateHCID 69545433HCID 69545433, compound

Product 1

HCID 69589137HCID 69589137, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-amino-3-[1-(pyrrol-2-yl)ethylidene]indolin-2-one (360 mg, 1.5 mmol) in tetrahydrofuran (15 mL) was treated with ethyl isocyanatoacetate (195 mg, 1.5 mmol) at ambient temperature. After stirring overnight, methanol (5 mL) was added and the reaction was concentrated. Chromatography on SiO2 (7.2 g) using 1:2 hexane/ethyl acetate afforded 5-(N′-(ethoxycarbonylmethyl)ureido)-3-[1-(pyrrol-2-yl)ethylidene]indolin-2-one; 1H NMR (400 MHz, DMSO-d6) δ 1.32 (t, 3H), 2.82 (s, 3H), 3.96 (d, 2H), 4.22 (q, 2H), 6.44 (m, 2H), 6.88 (d, 1H), 7.16 (m, 1H), 7.28 (d, 1H), 7.40 (m, 1H), 7.96 (m, 1H), 8.76 (s, 1H), 11.02 (s, 1H) ppm; (200 mg).

Workup

  1. concentrationthe reaction was concentrated

Sources & evidence

ORD record
ord-0314a4b9f2a34d77b81c20f8411fba5b
Source dataset
uspto-grants-2006_09
Patent number
US07105563B2

Reaction notes

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