Methyl iodide → HCID 124138196, compound

HRID 1486951Notes

Reaction equation

HRID 1486951 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6](C(O)=O)=[C:5]2[NH:15][C@@H:16]1[CH2:20][CH2:19][C@@H:18]([O:21][CH3:22])[CH2:17]1.[Br:23][C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[N:30]=[CH:29][C:28](C(O)=O)=[C:27]2[NH:37][C@H:38]1[CH2:42][CH2:41][C@H:40]([O:43][CH3:44])[CH2:39]1.IC.[OH-:47].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)Cl.O>[Br:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:37]([CH3:27])[C:38](=[O:47])[N:15]([C@@H:16]4[CH2:20][CH2:19][C@@H:18]([O:21][CH3:22])[CH2:17]4)[C:5]=3[C:4]=2[CH:3]=1.[Br:23][C:24]1[CH:33]=[CH:32][C:31]2[N:30]=[CH:29][C:28]3[N:15]([CH3:5])[C:16](=[O:47])[N:37]([C@H:38]4[CH2:42][CH2:41][C@H:40]([O:43][CH3:44])[CH2:39]4)[C:27]=3[C:26]=2[CH:25]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 131736838HCID 131736838, compound

Product 1

HCID 124138196HCID 124138196, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 6-bromo-4-[[(1R,3R)-3-methoxycyclopentyl]amino]quinoline-3-carboxylic acid: 6-bromo-4-[[(1S,3S)-3-methoxycyclopentyl]amino]quinoline-3-carboxylic acid (1:1 mixture) (13 g, 35.8 mmol), tetrabutylammonium bromide (1.16 g, 3.60 mmol), iodomethane (7.645 g, 53.86 mmol) and sodium hydroxide (2.15 g, 53.75 mmol) in DCM (600 mL) and water (380 mL) was stirred at ambient temperature overnight. The resulting solution was concentrated under vacuum to remove the organics and the solids collected by filtration, washed with water (5×10 mL) and dried in a vacuum oven to afford the desired material (racemic mixture) (9.8 g, 73%) as a off-white solid. NMR Spectrum: 1H NMR (400 MHz, DMSO-d6) δ 1.81-1.87 (1H, m), 2.33-2.51 (4H, m), 2.45-2.51 (1H, m), 3.28 (3H, s), 3.49 (3H, s), 4.02-4.21 (1H, m), 5.40 (1H, p), 7.73 (1H, dd), 7.98 (1H, d), 8.35 (1H, d), 8.91 (1H, s). Mass Spectrum: m/z (ES+)[M+H]+=375.9.

Workup

  1. concentrationThe resulting solution was concentrated under vacuum
  2. customto remove the organics and the solids
  3. filtrationcollected by filtration
  4. washwashed with water (5×10 mL)
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-94e47fb424e04af9a081e66068df7979
Source dataset
uspto-grants-2016_08
Patent number
US09428503B2

Reaction notes

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