p-Toluidine → HCID 15480078, compound

HRID 378714Notes

Reaction equation

HRID 378714 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:28][C:29]([OH:31])=O)([NH:17][C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][CH:22]=2)=[O:19])[C:9]1=[O:32])C1C=CC=CC=1.ON1[C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][C:37]=2N=N1.C(N(C(C)C)CC)(C)C.Cl.C(N=C=NCCCN(C)C)C.[NH2:64][C:65]1[CH:70]=[CH:69][C:68]([CH3:71])=[CH:67][CH:66]=1>CN(C)C=O>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:28][C:29]([NH:64][C:65]2[CH:70]=[CH:69][C:68]([CH3:71])=[CH:67][CH:66]=2)=[O:31])([NH:17][C:18]([NH:20][C:21]2[CH:22]=[CH:23][C:24]([CH3:27])=[CH:25][CH:26]=2)=[O:19])[C:9]1=[O:32])[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

7

Reactant 5

HCID 7813p-ToluidineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 15480077HCID 15480077, compound

Product 1

HCID 15480078HCID 15480078, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(RS)-1-Benzyl-3-(hydroxycarbonylmethyl)-3-(N'-(4-methylphenyl)ureido)indolin-2-one was dissolved in 15 ml of dry N,N-dimethylformamide, and 0.080 g of 1-hydroxybenzotriazole, 0.1 ml of diisopropylethylamine, 0.111 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride, and 0.065 g of p-toluidine were successively added to the solution. The mixture was stirred for 6 hours and concentrated. The concentrate was diluted with ethyl acetate and washed successively with dilute hydrochloric acid and a saturated aqueous solution of sodium hydrogencarbonate. The organic layer was dried over anhydrous sodium sulfate and concentrated. The crude product was purified by silica gel column chromatography (chloroform/ethyl acetate=4/1) to give 0.350 g (57%) of the title compound as a white powder.

Workup

  1. concentrationconcentrated
  2. additionThe concentrate was diluted with ethyl acetate
  3. washwashed successively with dilute hydrochloric acid
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified by silica gel column chromatography (chloroform/ethyl acetate=4/1)

Sources & evidence

ORD record
ord-c673574266fc4f34b81dceefce7a77db
Source dataset
uspto-grants-2000_02
Patent number
US06031111

Reaction notes

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