Hydrochloric Acid → HCID 18404695, compound

HRID 1017997Notes

Reaction equation

HRID 1017997 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([OH:23])=O)[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].ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.C(N(C(C)C)CC)(C)C.[I:54][C:55]1[CH:61]=[CH:60][C:58]([NH2:59])=[CH:57][CH:56]=1.Cl>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]([NH:59][C:58]2[CH:60]=[CH:61][C:55]([I:54])=[CH:56][CH:57]=2)=[O:23])[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]

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 108934-IodoanilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 114498403-Methoxy-4-o-tolylureidophenylacetic acid

Product 1

HCID 18404695HCID 18404695, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 3-methoxy-4-[3-(2-methylphenyl)ureido]phenylacetic acid (2.9 g, Reference Example 31), 1-hydroxybenzotriazole (2.13 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (2.67 g) and diisopropylethylamine (3.6 g) in anhydrous dimethylformamide (30 ml) was treated with 4-iodoaniline (2.43 g). After stirring at ambient temperature for 18 hours the reaction mixture was poured into a mixture of ethyl acetate (50 ml) and hydrochloric acid (50 ml, 1M). The resultant solid was filtered and then 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 (4.05 g) as a light brown solid, m.p. >200° C.

Workup

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

Sources & evidence

ORD record
ord-dd27248754f9436bae56fb1aa78e9075
Source dataset
uspto-grants-2002_11
Patent number
US06479519B1

Reaction notes

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