Hydrochloric Acid → HCID 60151297, compound

HRID 2409972Notes

Reaction equation

HRID 2409972 reaction equation
[CH3:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH2:17][C:18]3[N:23]=[C:22]([C:24]([OH:26])=O)[CH:21]=[CH:20][CH:19]=3)=[C:7]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[NH:8]2)=[CH:4][CH:3]=1.[CH3:27][S:28]([NH2:31])(=[O:30])=[O:29].Cl.C(N=C=NCCCN(C)C)C.Cl>ClCCl.CN(C)C1C=CN=CC=1>[CH3:27][S:28]([NH:31][C:24]([C:22]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:17][C:6]2[C:5]3[C:9](=[CH:10][C:2]([CH3:1])=[CH:3][CH:4]=3)[NH:8][C:7]=2[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:23]=1)=[O:26])(=[O:30])=[O:29]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 50902001HCID 50902001, compound

Product 1

HCID 60151297HCID 60151297, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Under an argon atmosphere, to a solution of 6-(6-methyl-2-phenyl-1H-indol-3-ylmethyl)pyridine-2-carboxylic acid (838 mg) in dichloromethane (17.4 mL) were added methane sulfonamide (279 mg), 4-dimethylaminopyridine (718 mg), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.13 g) successively, and this mixture was stirred at room temperature for 24 hours. To the reaction mixture was added 1 mol/L hydrochloric acid, followed by extraction with dichloromethane. The organic layer was washed with 1 mol/L hydrochloric acid, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: methanol-dichloromethane) to obtain the title compound (740 mg).

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. washThe organic layer was washed with 1 mol/L hydrochloric acid
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluting solvent: methanol-dichloromethane)

Sources & evidence

ORD record
ord-a3d8aef060744d7daeb5fc47ad6ebf30
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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