Methyl iodide → trans-N-(7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoro-N-methylacetamide

HRID 16157Notes

Reaction equation

HRID 16157 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:29]=[CH:28][C:7]2[O:8][C:9]3[CH:27]=[CH:26][CH:25]=[CH:24][C:10]=3[C@@H:11]3[C@H:16]([NH:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[CH2:15][CH2:14][CH2:13][N:12]3[C:6]=2[CH:5]=1.[CH3:30]I>CN(C=O)C>[Cl:3][C:4]1[CH:29]=[CH:28][C:7]2[O:8][C:9]3[CH:27]=[CH:26][CH:25]=[CH:24][C:10]=3[C@@H:11]3[C@H:16]([N:17]([CH3:30])[C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])[CH2:15][CH2:14][CH2:13][N:12]3[C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86599857trans-N-(7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide

Product 1

HCID 86599865trans-N-(7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoro-N-methylacetamideYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (1.6 mg, 60% in oil) was added to trans-N-(7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoroacetamide (15 mg, 0.04 mmol) in 1 mL of DMF. After 10 minutes stirring methyl iodide (2.47 μL, 0.04 mmol) was added. The resulting mixture was stirred at room temperature for 18 h. After evaporation the crude compound was purified by chromatography on silica. Elution with toluene/ethyl acetate 7:3 gave trans-N-(7-chloro-2,3,4,14b-tetrahydro-1H-dibenzo[b,f]pyrido[1,2-d][1,4]oxazepin-1-yl)-2,2,2-trifluoro-N-methylacetamide (14 mg, 90%). Data: (m/z)=411 (M+H)+.

Workup

  1. additionwas added
  2. customAfter evaporation the crude compound
  3. customwas purified by chromatography on silica
  4. washElution with toluene/ethyl acetate 7:3

Sources & evidence

ORD record
ord-393d1ff41ac04fe6a2345fb0ec1318af
Source dataset
uspto-grants-2010_06
Patent number
US07737136B2

Reaction notes

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