3-Methyl-2-furoic acid → HCID 121254625, compound

HRID 530436Notes

Reaction equation

HRID 530436 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:7]2[N:8]([C:16]([NH2:18])=[O:17])[C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[S:5][CH:6]=1.[CH3:19][C:20]1[CH:24]=[CH:23][O:22][C:21]=1[C:25](O)=[O:26].Cl.CN(C)CCCN=C=NCC>ClCCCl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[CH3:19][C:20]1[CH:24]=[CH:23][O:22][C:21]=1[C:25]([NH:1][C:2]1[CH:3]=[C:4]([C:7]2[N:8]([C:16]([NH2:18])=[O:17])[C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[S:5][CH:6]=1)=[O:26]

Participants

7

Reactant 3

HCID 781273-Methyl-2-furoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 121254619HCID 121254619, compound

Product 1

HCID 121254625HCID 121254625, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To the solution of 2-(4-amino-2-thienyl)-1H-indole-1-carboxamide (51.4 mg, 0.2 mmol, 1 eq) and 3-methyl-furan-2-carboxylic acid (25.2 mg, 1 eq) in anhydrous DCE (2 mL) was added 4-(dimethylamino)pyridine (4.9 mg, 0.2 eq) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (46.1 mg, 1.2 eq). After the reaction was stirred at 60° C. for 1 hour, it was diluted with ethyl acetate, washed sequentially with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, brine, and lastly dried with anhydrous sodium sulfate. The upper clear solution was decanted, concentrated, and the oily residue was subject to a gradient column chromatography (EtOAc-Hex 1:100 to 1:2) to yield 2-{4-[(3-methyl-2-furoyl)amino]-2-thienyl}-1H-indole-1-carboxamide as a yellow solid in amount of 42 mg.

Workup

  1. washwashed sequentially with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, brine
  2. dry with materiallastly dried with anhydrous sodium sulfate
  3. customThe upper clear solution was decanted
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-abf1dc9221da4af0aed6ff154c506e33
Source dataset
uspto-grants-2016_05
Patent number
US09353093B2

Reaction notes

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