Hydrochloric Acid → HCID 68535611, compound

HRID 2389333Notes

Reaction equation

HRID 2389333 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[CH:9]=[C:8]([CH:10]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]=[CH:6][C:5]1=[O:23].[NH:24]1[C:32]2[CH:31]=[CH:30][CH:29]=[C:28]([C:33](O)=[O:34])[C:27]=2[CH:26]=[CH:25]1.C1C=CC2N(O)N=NC=2C=1.Cl>O.CN(C=O)C>[C:11]1([CH:10]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:8]2[CH:7]=[CH:6][C:5](=[O:23])[N:4]([CH2:3][CH2:2][NH:1][C:33]([C:28]3[C:27]4[CH:26]=[CH:25][NH:24][C:32]=4[CH:31]=[CH:30][CH:29]=3)=[O:34])[CH:9]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 595229Indole-4-carboxylic acidHCID 68533639HCID 68533639, compound

Product 1

HCID 68535611HCID 68535611, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-(2-aminoethyl)-5-(diphenylmethyl)-2(1H)-pyridinone (75.0 mg), a mixture of indole-4-carboxylic acid (39.7 mg), HOBt (36.6 mg) and DMF (3.0 mL) was added WSCD. HCl (52.0 mg) at ambient temperature and the mixture was stirred at the same temperature for 18 hours. The resulting mixture was diluted with water (10.0 mL) and extracted with EtOAc (15 mL). The organic layer was washed successively with 1M HCl aqueous solution, saturated NaHCO3 aqueous solution and brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo. The residue was purified by preparative thin-layer chromatography (chloroform:MeOH=90:10) to afford N-{2-[5-(diphenylmethyl)-2-oxo-1(2H)-pyridinyl]ethyl}-1H-indole-4-carboxamide (65 mg) as a yellow amorphous powder.

Workup

  1. additionwas added WSCD
  2. extractionextracted with EtOAc (15 mL)
  3. washThe organic layer was washed successively with 1M HCl aqueous solution, saturated NaHCO3 aqueous solution and brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customThe residue was purified by preparative thin-layer chromatography (chloroform:MeOH=90:10)

Sources & evidence

ORD record
ord-e17263b8fc7f4a1da7f56c92e81875f4
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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