Hydrochloric Acid → HCID 60141999, compound

HRID 2400282Notes

Reaction equation

HRID 2400282 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][C:13]1[N:18]=[C:17]([C:19](O)=[O:20])[CH:16]=[CH:15][CH:14]=1)[C:7]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[CH:6]2.[CH3:28][S:29]([NH2:32])(=[O:31])=[O:30].Cl.C(N=C=NCCCN(C)C)C.Cl>ClCCl.CN(C)C1C=CN=CC=1>[CH3:28][S:29]([NH:32][C:19]([C:17]1[CH:16]=[CH:15][CH:14]=[C:13]([CH2:12][N:8]2[C:9]3[C:5](=[CH:4][C:3]([O:2][CH3:1])=[CH:11][CH:10]=3)[CH:6]=[C:7]2[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:18]=1)=[O:20])(=[O:31])=[O:30]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 50907648HCID 50907648, compound

Product 1

HCID 60141999HCID 60141999, compoundYield 15.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Under an argon atmosphere, to a solution of 6-(5-methoxy-2-phenylindol-1-ylmethyl)pyridine-2-carboxylic acid (84 mg) in dichloromethane (2.3 mL) were added methanesulfonamide (22 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (45 mg), and 4-dimethylaminopyridine (29 mg). This mixture was stirred for 66 hours at room temperature. To the reaction mixture, 1 mol/L hydrochloric acid was added and stirred vigorously. The organic layer was separated, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: dichloromethane-methanol). The solvent was removed under reduced pressure. The residue was recrystallized from ethanol to obtain the title compound (16 mg). 1H-NMR (CDCl3) δ ppm: 3.38 (3H, s), 3.87 (3H, s), 5.49 (2H, s), 6.64 (1H, d, J=0.5 Hz), 6.84 (1H, dd, J=2.4, 8.9 Hz), 6.90-6.95 (1H, m), 7.05 (1H, d, J=8.9 Hz), 7.16 (1H, d, J=2.4 Hz), 7.30-7.50 (5H, m), 7.76 (1H, t, J=7.8 Hz), 8.00-8.10 (1H, m), 10.01 (1H, br s).

Workup

  1. stirringstirred vigorously
  2. customThe organic layer was separated
  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: dichloromethane-methanol)
  6. customThe solvent was removed under reduced pressure
  7. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-23342013a8c149c6a6104635a5e1125d
Source dataset
uspto-grants-2014_08
Patent number
US08796247B2

Reaction notes

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