Methyl iodide → HCID 57006595, compound

HRID 1375013Notes

Reaction equation

HRID 1375013 reaction equation
[F:1][C:2]([F:48])([F:47])[C:3]1[CH:4]=[C:5]([CH:40]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:42]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][O:19][C@H:18]([CH2:22][O:23][CH3:24])[CH2:17]2)[CH2:10][C@H:9]1[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[C:28]([NH:33][C:34](=[O:39])[C:35]([F:38])([F:37])[F:36])[CH:27]=1)=[O:7].[H-].[Na+].[CH3:51]I>O1CCCC1.[Cl-].[Na+].O>[F:48][C:2]([F:1])([F:47])[C:3]1[CH:4]=[C:5]([CH:40]=[C:41]([C:43]([F:45])([F:46])[F:44])[CH:42]=1)[C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][O:19][C@H:18]([CH2:22][O:23][CH3:24])[CH2:17]2)[CH2:10][C@H:9]1[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[C:28]([N:33]([CH3:51])[C:34](=[O:39])[C:35]([F:38])([F:37])[F:36])[CH:27]=1)=[O:7]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57074082HCID 57074082, compound

Product 1

HCID 57006595HCID 57006595, compoundYield 23.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of (2R)-1-[3,5-bis(trifluoromethyl)-benzoyl]-2-[4-methyl-3-(trifluoroacetylamino)benzyl]-4-[2-[(2S)-2-(methoxymethyl)morpholino]ethyl]piperazine (131 mg) in tetrahydrofuran (2 ml) was added sodium hydride (10 mg) and the resulting mixture was stirred for 20 minutes. Methyl iodide (28 mg) was added to the mixture and the whole was stirred at room temperature overnight. Brine was added to the mixture and the organic layer was separated, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by HPLC to give (2R)-1-[3,5-bis(trifluoromethyl)benzoyl]-2-[4-methyl-3-(N-methyl-N-trifluoroacetylamino)benzyl]-4-[2-[(2S)-2-(methoxymethyl)-morpholino]ethyl]piperazine (31 mg) as an oil. The obtained compound was converted to its dihydrochloride in a conventional manner.

Workup

  1. stirringthe whole was stirred at room temperature overnight
  2. customthe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-ed6a5ece6c2f4b69aeb35eab66402aa5
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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