5-Formyl-2-thiophenecarboxylic Acid → HCID 118142901, compound

HRID 2279928Notes

Reaction equation

HRID 2279928 reaction equation
[CH:1]([C:3]1[S:7][C:6]([C:8]([OH:10])=[O:9])=[CH:5][CH:4]=1)=[O:2].[Cl:11][C:12]1[CH:13]=[N+:14]([O-:32])[CH:15]=[C:16]([Cl:31])[C:17]=1[CH2:18][C@@H:19]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1)O.Cl.CN(C)CCCN=C=NCC>ClCCl.CN(C)C1C=CN=CC=1>[Cl:31][C:16]1[CH:15]=[N+:14]([O-:32])[CH:13]=[C:12]([Cl:11])[C:17]=1[CH2:18][C@H:19]([O:9][C:8]([C:6]1[S:7][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=1)=[O:10])[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1

Participants

6

Reactant 3

HCID 8188825-Formyl-2-thiophenecarboxylic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 71092494(S)-3,5-dichloro-4-(2-(3,4-dimethoxyphenyl)-2-hydroxyethyl)pyridine 1-oxide

Product 1

HCID 118142901HCID 118142901, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 5-formyl-2-thiophenecarboxylic acid (400 mg, 2.56 mmol) in dichloromethane (20 mL) was added with (1S)-2-(3,5-dichloro-1-oxido-pyridin-1-ium-4-yl)-1-(3,4-dimethoxyphenyl)ethanol I-1/A (881 mg, 2.56 mmol) followed by 4-(dimethylamino)-pyridine (156 mg, 1.28 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (983 mg, 5.12 mmol). The resulting mixture was stirred at room temperature for 18 h. The reaction was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution. The organic layer was washed with brine, passed through a hydrophobic fit and the solvent was removed in vacuo. The crude material was purified by silica gel column chromatography, eluting with 0-100% EtOAc in DCM, to afford the title compound (488 mg, 39%) as yellow oil.

Workup

  1. customThe reaction was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution
  2. washThe organic layer was washed with brine
  3. customthe solvent was removed in vacuo
  4. customThe crude material was purified by silica gel column chromatography
  5. washeluting with 0-100% EtOAc in DCM

Sources & evidence

ORD record
ord-f0fad00b73da4ee2be51b0d4ad6abcfa
Source dataset
uspto-grants-2015_09
Patent number
US09133185B2

Reaction notes

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