Water → HCID 131726464, compound

HRID 2426643Notes

Reaction equation

HRID 2426643 reaction equation
[C:1]([CH2:4][NH:5][C@@H:6]1[CH2:10][CH2:9][N:8]([C:11]2[CH:16]=[CH:15][C:14]([NH:17][C:18]([N:20]3[CH2:25][CH2:24][CH:23]([C:26]4[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=4)[CH2:22][CH2:21]3)=[O:19])=[CH:13][CH:12]=2)[CH2:7]1)(=[O:3])[CH3:2].[H-].[Na+].I[CH3:36].O>CN(C=O)C>[C:1]([CH2:4][NH:5][C@@H:6]1[CH2:10][CH2:9][N:8]([C:11]2[CH:12]=[CH:13][C:14]([N:17]([CH3:36])[C:18]([N:20]3[CH2:21][CH2:22][CH:23]([C:26]4[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=4)[CH2:24][CH2:25]3)=[O:19])=[CH:15][CH:16]=2)[CH2:7]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 131726465HCID 131726465, compound

Product 1

HCID 131726464HCID 131726464, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(R)-4-(4-Fluorophenyl)piperidine-1-carboxylic acid {4-[3-(acetylmethyl -amino)pyrrolidin-1-yl]phenyl}amide (22 mg) was added to a suspension of sodium hydride (95% in oil; 0.005 g) in DMF (1 ml). After evolution of gas ceased, iodomethane (0.02 ml) was added. After two hours, the reaction mixture was cautiously hydrolyzed with water and extracted with dichloromethane. The organic phase was dried over magnesium sulfate and concentrated, and the residue was crystallized from pentane. This resulted in the product with the molecular weight of 452,58 (C26H33FN4O2); MS (ESI): 453 (M+H+).

Workup

  1. extractionextracted with dichloromethane
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customthe residue was crystallized from pentane
  5. customThis resulted in the product with the molecular weight of 452,58 (C26H33FN4O2)

Sources & evidence

ORD record
ord-9e45f80a9680410ab95a661daeb211bd
Source dataset
uspto-grants-2011_06
Patent number
US07968550B2

Reaction notes

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