Hydrochloric Acid → HCID 86703293, compound

HRID 2409979Notes

Reaction equation

HRID 2409979 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:18][C:19]3[N:24]=[C:23]([C:25](O)=[O:26])[CH:22]=[CH:21][CH:20]=3)=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:9]2)=[CH:5][CH:4]=1.[N:28]#[C:29][NH2:30].Cl.C(N=C=NCCCN(C)C)C.Cl>ClCCl.CN(C)C1C=CN=CC=1>[C:29]([NH:30][C:25]([C:23]1[CH:22]=[CH:21][CH:20]=[C:19]([CH2:18][C:7]2[C:6]3[C:10](=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[NH:9][C:8]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:24]=1)=[O:26])#[N:28]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9864CyanamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 50903301HCID 50903301, compound

Product 1

HCID 86703293HCID 86703293, compoundYield 68.5%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Under an argon atmosphere, to a suspension of 6-(6-methoxy-2-phenyl-1H-indol-3-ylmethyl)pyridine-2-carboxylic acid (100 mg) in dichloromethane (2.8 mL) were added cyanamide (12.9 mg), 4-dimethylaminopyridine (75 mg), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (118 mg) successively, and this mixture was stirred at room temperature for 60 hours. To the reaction mixture was added 1 mol/L hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with 1 mol/L hydrochloric acid, water, and saturated brine successively, 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 (73.1 mg). 1H-NMR (DMSO-d6) δ ppm: 3.78 (3H, s), 4.47 (2H, s), 6.64 (1H, dd, J=2.3, 8.8 Hz), 6.89 (1H, d, J=2.3 Hz), 7.18-7.39 (3H, m), 7.42-7.52 (2H, m), 7.56-7.68 (2H, m), 7.84-7.99 (2H, m), 11.24 (1H, s). ESI-MS (m/z): 383 (M+H)+

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with 1 mol/L hydrochloric acid, water, and saturated brine successively
  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-b9b97898957842629ce8351ff640d36d
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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