2-Thiophenecarboxylic acid → HCID 68533883, compound

HRID 644265Notes

Reaction equation

HRID 644265 reaction equation
[NH2:1][CH2:2][CH2:3][O:4][C:5]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:6]=1[C:7]([NH:9][C:10]1[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:11]=1[C:12]([NH:14][C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=1)=[O:13])=[O:8].[S:36]1[CH:40]=[CH:39][CH:38]=[C:37]1[C:41](O)=[O:42]>C(Cl)Cl>[CH3:35][O:34][C:32]1[CH:31]=[CH:30][C:6]([C:7]([NH:9][C:10]2[CH:26]=[C:25]([N+:27]([O-:29])=[O:28])[CH:24]=[CH:23][C:11]=2[C:12]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[O:13])=[O:8])=[C:5]([O:4][CH2:3][CH2:2][NH:1][C:41]([C:37]2[S:36][CH:40]=[CH:39][CH:38]=2)=[O:42])[CH:33]=1

Participants

4

Reactant 2

HCID 107002-Thiophenecarboxylic acidHCID 57860820HCID 57860820, compound

Product 1

HCID 68533883HCID 68533883, compoundYield 95.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-[2-(2-aminoethoxy)-4-methoxybenzoylamino]-N-(4-methoxy-phenyl)-4-nitrobenzamide (227 mg, 0.47 mmol), P-EPC resin (2.09 g, 1.78 mmol), and thiophene-2-carboxylic acid (144 mg, 1.12 mmol) in methylene chloride (15 mL) was shaken in a screw top vial overnight. The reaction was filtered and the solids were washed with 10% methanol in chloroform. The filtrate was concentrated to yield the desired product (265 mg, 0.45 mmol, 95%) as a greenish solid.

Workup

  1. filtrationThe reaction was filtered
  2. washthe solids were washed with 10% methanol in chloroform
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-653683ebf15a4aa894ecb53c9e073a27
Source dataset
uspto-grants-2010_04
Patent number
US07700628B2

Reaction notes

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