Methyl iodide → HCID 23729291, compound

HRID 1911782Notes

Reaction equation

HRID 1911782 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]=[C:16]2[N:31]=[C:30]([CH3:32])[N:29]([CH3:33])[C:17]2=[N:18][C:19]=1[N:20]([CH2:25][CH:26]1[CH2:28][CH2:27]1)[CH2:21][CH:22]1[CH2:24][CH2:23]1)[C:8]1[N:9]=[N:10][NH:11][N:12]=1.[H-].[Na+].CI.[C:47](OCC)(=O)C>CN(C=O)C>[F:42][C:2]([F:41])([F:1])[C:3]1[CH:4]=[C:5]([CH:34]=[C:35]([C:37]([F:38])([F:39])[F:40])[CH:36]=1)[CH2:6][N:7]([CH2:13][C:14]1[CH:15]=[C:16]2[N:31]=[C:30]([CH3:32])[N:29]([CH3:33])[C:17]2=[N:18][C:19]=1[N:20]([CH2:25][CH:26]1[CH2:28][CH2:27]1)[CH2:21][CH:22]1[CH2:24][CH2:23]1)[C:8]1[N:12]=[N:11][N:10]([CH3:47])[N:9]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 58795834HCID 58795834, compound

Product 1

HCID 23729291HCID 23729291, compoundYield 4.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (6-{[(3,5-bis-trifluoromethyl-benzyl)-(2H-tetrazol-5-yl)-amino]-methyl}-2,3-dimethyl-3H-imidazo[4,5-b]pyridin-5-yl)-bis-cyclopropylmethyl-amine (0.220 g, 3.7 mmol.) in DMF (8 mL) was added 60% sodium hydride (0.017 g, 0.741 mmol.) at 0° C. and the resulting reaction mixture was stirred at the same temperature for 15 min. and then methyl iodide (0.046 mL, 0.0741 mmol.) was added and continued to stir for 30 min. The crude product was extracted with ethyl acetate (250 mL), washed with water (250 mL×2) and the organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by column chromatography using 230-400 mesh silica gel eluting with 1:1 hexane: ethyl acetate yielded 0.010 gm (yield: 4.4%) of pure colorless gummy compound.

Workup

  1. customthe resulting reaction mixture
  2. stirringto stir for 30 min
  3. extractionThe crude product was extracted with ethyl acetate (250 mL)
  4. washwashed with water (250 mL×2)
  5. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customPurification by column chromatography

Sources & evidence

ORD record
ord-3832632c02ee42cb81112a08c390c9d3
Source dataset
uspto-grants-2013_12
Patent number
US08604055B2

Reaction notes

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