Hydrochloric Acid → HCID 54055857, compound

HRID 1017996Notes

Reaction equation

HRID 1017996 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([NH:23][C:24]2[CH:29]=[CH:28][C:27](I)=[CH:26][CH:25]=2)=[O:22])[CH:6]=[CH:7][C:8]=1[NH:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH3:19])=[O:11].C(N(CCCC)CCCC)CCC.[C:44]([O:48][C:49]([CH3:52])([CH3:51])[CH3:50])(=[O:47])[CH:45]=[CH2:46].Cl>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(OCC)(=O)C>[C:49]([O:48][C:44](=[O:47])[CH:45]=[CH:46][C:27]1[CH:28]=[CH:29][C:24]([NH:23][C:21](=[O:22])[CH2:20][C:5]2[CH:6]=[CH:7][C:8]([NH:9][C:10]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[CH3:19])=[O:11])=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:25][CH:26]=1)([CH3:52])([CH3:51])[CH3:50]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 7622TributylamineHCID 15458tert-Butyl acrylateHCID 18404695HCID 18404695, compound

Product 1

HCID 54055857HCID 54055857, compoundYield 90%

Reagents, catalysts & solvents 4

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-{3-methoxy-4-[3-(2-methylphenyl)ureido]phenylacetylamino}-iodobenzene [4.0 g, Reference Example 9(a)], palladium acetate (50 mg), tri-(o-tolyl)phosphine (125 mg) and tributylamine (1.85 g) in anhydrous dimethylformamide (10 ml) was treated with tert-butyl acrylate (1.0 g). The reaction mixture was stirred at 100° C. under an atmosphere of nitrogen for 4 hours then cooled to room temperature and then poured into a mixture of ethyl acetate (50 ml) and hydrochloric acid (50 ml, 1M). The resultant solid was filtered and washed sequentially with 50 ml portions of saturated aqueous sodium bicarbonate solution, water and diethyl ether. The residue was dried under vacuum to give the title compound (3.6 g) as a white solid.

Workup

  1. temperaturethen cooled to room temperature
  2. filtrationThe resultant solid was filtered
  3. washwashed sequentially with 50 ml portions of saturated aqueous sodium bicarbonate solution, water and diethyl ether
  4. customThe residue was dried under vacuum

Sources & evidence

ORD record
ord-e906ca7f838c4126ab0d9ee0d6252093
Source dataset
uspto-grants-2002_11
Patent number
US06479519B1

Reaction notes

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