Hydrochloric Acid → HCID 86707951, compound

HRID 2400298Notes

Reaction equation

HRID 2400298 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[N:10]([CH2:20][C:21]2[N:26]=[C:25]([C:27]([OH:29])=O)[CH:24]=[CH:23][CH:22]=2)[C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([O:18][CH3:19])=[CH:13][CH:12]=2.[N:30]#[C:31][NH2:32].Cl.C(N=C=NCCCN(C)C)C.Cl>ClCCl.CN(C)C1C=CN=CC=1>[C:31]([NH:32][C:27]([C:25]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:20][N:10]2[C:11]3[C:16](=[CH:15][C:14]([O:18][CH3:19])=[CH:13][CH:12]=3)[CH:17]=[C:9]2[C:3]2[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=2[F:1])[N:26]=1)=[O:29])#[N:30]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9864CyanamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 50908089HCID 50908089, compound

Product 1

HCID 86707951HCID 86707951, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-[2-(2,5-difluorophenyl)-5-methoxyindol-1-ylmethyl]pyridine-2-carboxylic acid (70 mg) in dichloromethane (1.8 mL) were successively added cyanamide (8.2 mg), 4-dimethylaminopyridine (48 mg), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (75 mg). This mixture was stirred for 35 hours at room temperature. 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 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: ethyl acetate-methanol) to obtain the title compound (55 mg). 1H-NMR (DMSO-d6) δ ppm: 3.77 (3H, s), 5.37 (2H, s), 6.45 (1H, d, J=7.4 Hz), 6.66 (1H, s), 6.79 (1H, dd, J=2.4, 8.9 Hz), 7.10-7.45 (4H, m), 7.50-7.85 (3H, m). ESI-MS (m/z): 419 (M+H)+

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. washThe organic layer was washed with 1 mol/L hydrochloric acid 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: ethyl acetate-methanol)

Sources & evidence

ORD record
ord-89a033021985443789d58c151583c110
Source dataset
uspto-grants-2014_08
Patent number
US08796247B2

Reaction notes

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