Methyl 4-aminobenzoate → HCID 25189526, compound

HRID 1023713Notes

Reaction equation

HRID 1023713 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([C:12]([OH:14])=O)[NH:7][C:8]=1[CH:9]([CH3:11])[CH3:10])([CH3:3])[CH3:2].[NH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22]C)=[O:21])=[CH:18][CH:17]=1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[CH:1]([C:4]1[CH:5]=[C:6]([C:12]([NH:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=2)=[O:14])[NH:7][C:8]=1[CH:9]([CH3:10])[CH3:11])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 12082Methyl 4-aminobenzoateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58420547HCID 58420547, compound

Product 1

HCID 25189526HCID 25189526, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4,5-diisopropylpyrrole-2-carboxylic acid (78 mg, 0.400 mmol) and methyl 4-aminobenzoate (181 mg, 1.20 mmol) in dichloromethane (5 ml) was added with 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (192 mg, 1.00 mmol) under an argon atmosphere, and the mixture was stirred at room temperature for 2 hours. The reaction mixture was treated in a conventional manner, and then the resultant was purified by silica gel chromatography (0.5% methanol-chloroform) to obtain the desired condensate (27 mg, 21%) from the low polarity portion, and the acid anhydride (30 mg, 40%), the starting material, from the high polarity portion.

Workup

  1. additionThe reaction mixture was treated in a conventional manner
  2. customthe resultant was purified by silica gel chromatography (0.5% methanol-chloroform)
  3. customto obtain the desired condensate (27 mg, 21%) from the low polarity portion

Sources & evidence

ORD record
ord-165ad1fa5cc14cd789f2a99604a8d15c
Source dataset
uspto-grants-2014_05
Patent number
US08722730B2

Reaction notes

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