Methyl iodide → HCID 23729277, compound

HRID 1911776Notes

Reaction equation

HRID 1911776 reaction equation
[F:1][C:2]([F:42])([F:41])[C:3]1[CH:4]=[C:5]([CH:34]=[C:35]([C:37]([F:40])([F:39])[F:38])[CH:36]=1)[CH2:6][N:7]([CH2:13][C:14]1[CH:15]=[N:16][C:17]2[C:22]([C:23]=1[N:24]([CH2:29][CH:30]1[CH2:32][CH2:31]1)[CH2:25][CH:26]1[CH2:28][CH2:27]1)=[CH:21][C:20]([CH3:33])=[CH:19][CH:18]=2)[C:8]1[N:9]=[N:10][NH:11][N:12]=1.[H-].[Na+].[CH3:45]I>CN(C=O)C.CCOC(C)=O>[F:38][C:37]([F:40])([F:39])[C:35]1[CH:34]=[C:5]([CH:4]=[C:3]([C:2]([F:41])([F:1])[F:42])[CH:36]=1)[CH2:6][N:7]([CH2:13][C:14]1[CH:15]=[N:16][C:17]2[C:22]([C:23]=1[N:24]([CH2:29][CH:30]1[CH2:31][CH2:32]1)[CH2:25][CH:26]1[CH2:27][CH2:28]1)=[CH:21][C:20]([CH3:33])=[CH:19][CH:18]=2)[C:8]1[N:9]=[N:10][N:11]([CH3:45])[N:12]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58795815HCID 58795815, compound

Product 1

HCID 23729277HCID 23729277, compoundYield 28.63%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of (3-{[(3,5-bis-trifluoromethyl-benzyl)-(2H-tetrazol-5-yl)-amino]-methyl}-6-methyl-quinolin-4-yl)-bis-cyclopropylmethyl-amine (700 mg, 1.18 mmol) and sodium hydride (60%) (61 mg, 1.5 mmol) in DMF (25 mL) was stirred at 0° C. for 5 min. To this, methyl iodide (337 g, 2 mmol) was then added and stirring was continued for another 30 min. The reaction mixture was diluted with EtOAc (200 mL) and washed with water (200 mL×4) and finally with brine (100 mL). The organic layer was separated, dried over sodium sulphate and concentrated under vacuum. The crude product was purified by column chromatography (silica gel 230-400 mesh). Elution with 1.5% EtOAc in hexane afforded 0.205 gm of gummy mass (yield: 28.63%).

Workup

  1. stirringstirring
  2. waitwas continued for another 30 min
  3. washwashed with water (200 mL×4) and finally with brine (100 mL)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated under vacuum
  7. customThe crude product was purified by column chromatography (silica gel 230-400 mesh)
  8. washElution with 1.5% EtOAc in hexane
  9. customafforded 0.205 gm of gummy mass (yield: 28.63%)

Sources & evidence

ORD record
ord-18980f954f27402086a062bc079005c8
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

Loading…