Hydrochloric Acid → HCID 86703274, compound

HRID 2409949Notes

Reaction equation

HRID 2409949 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[CH:17]=3)[C:12]([CH2:21][C:22]3[N:27]=[C:26]([C:28]([OH:30])=O)[CH:25]=[CH:24][CH:23]=3)=[C:11]2[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:37][S:38]([NH2:41])(=[O:40])=[O:39].Cl.C(N=C=NCCCN(C)C)C.Cl>ClCCl.CN(C)C1C=CN=CC=1>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[C:16]([O:19][CH3:20])[CH:17]=3)[C:12]([CH2:21][C:22]3[N:27]=[C:26]([C:28]([NH:41][S:38]([CH3:37])(=[O:40])=[O:39])=[O:30])[CH:25]=[CH:24][CH:23]=3)=[C:11]2[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86703273HCID 86703273, compound

Product 1

HCID 86703274HCID 86703274, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(1-benzenesulfonyl-6-methoxy-2-phenyl-1H-indol-3-ylmethyl)pyridine-2-carboxylic acid (867 mg) in dichloromethane (17.4 mL) were added methanesulfonamide (199 mg), 4-dimethylaminopyridine (510 mg), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (800 mg) 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 (633 mg). 1H-NMR (DMSO-d6) δ ppm: 3.39 (3H, s), 3.86 (3H, s), 4.03 (2H, s), 6.85-6.98 (2H, m), 7.37 (1H, d, J=8.8 Hz), 7.39-7.53 (9H, m), 7.60-7.71 (2H, m), 7.77-7.88 (2H, m), 11.00-11.56 (1H, br). ESI-MS (m/z): 576 (M+H)+

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-7e0f77cbaef74cf99fa205b40ffe3721
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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