Dimethyl Sulfoxide → 3-[1-(4-carbamoyl-2-methylphenyl)-5-(4-ureidophenyl)-1H-pyrrol-2-yl]-propionic acid ethyl ester

HRID 2362212Notes

Reaction equation

HRID 2362212 reaction equation
[OH-].[NH4+:2].[CH2:3]([O:5][C:6](=[O:40])[CH2:7][CH2:8][C:9]1[N:10]([C:30]2[CH:35]=[CH:34][C:33]([C:36](=[O:38])[NH2:37])=[CH:32][C:31]=2[CH3:39])[C:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([O:23]C3C=CC=CC=3)=O)=[CH:16][CH:15]=2)=[CH:12][CH:13]=1)[CH3:4].CS(C)=O>O>[CH2:3]([O:5][C:6](=[O:40])[CH2:7][CH2:8][C:9]1[N:10]([C:30]2[CH:35]=[CH:34][C:33]([C:36](=[O:38])[NH2:37])=[CH:32][C:31]=2[CH3:39])[C:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20][C:21]([NH2:2])=[O:23])=[CH:16][CH:15]=2)=[CH:12][CH:13]=1)[CH3:4]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 14923Ammonium HydroxideHCID 583056243-[1-(4-carbamoyl-2-methylphenyl)-5-(4-phenoxycarbonylaminophenyl)-1H-pyrrol-2-yl]-propionic acid ethyl ester

Product 1

HCID 583057813-[1-(4-carbamoyl-2-methylphenyl)-5-(4-ureidophenyl)-1H-pyrrol-2-yl]-propionic acid ethyl esterYield 35%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

Under a nitrogen atmosphere, ammonium hydroxide (2 mL) was slowly added to 3-[1-(4-carbamoyl-2-methylphenyl)-5-(4-phenoxycarbonylaminophenyl)-1H-pyrrol-2-yl]-propionic acid ethyl ester (13B) (66 mg, 0.13 mmol). Dimethylsulfoxide (1 mL) was slowly added. The reaction was then heated to 85° C. for 24 hrs. After cooling, the reaction was diluted with water and extracted with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by preparative TLC plate (1500 microns, 10% IPA/CH2Cl2). The desired band (rf=0.2) was isolated and dried under high vacuum to yield 3-[1-(4-carbamoyl-2-methylphenyl)-5-(4-ureidophenyl)-1H-pyrrol-2-yl]-propionic acid ethyl ester (13C) (20 mg, 35%, light yellow powder).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by preparative TLC plate (1500 microns, 10% IPA/CH2Cl2)
  7. customThe desired band (rf=0.2) was isolated
  8. customdried under high vacuum

Sources & evidence

ORD record
ord-3e6362ecb6d24e73904abd6a2d84679e
Source dataset
uspto-grants-2014_04
Patent number
US08691816B2

Reaction notes

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