Methyl iodide → HCID 59382273, compound

HRID 425185Notes

Reaction equation

HRID 425185 reaction equation
[CH2:1]([O:8][C:9]1[CH:30]=[C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:28]([C:39]([CH3:41])=[CH2:40])=[CH:27][C:10]=1[C:11]([NH:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[CH:16][CH:15]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:44]I>CN(C=O)C.CCOC(C)=O.O>[CH2:1]([O:8][C:9]1[CH:30]=[C:29]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:28]([C:39]([CH3:41])=[CH2:40])=[CH:27][C:10]=1[C:11]([N:13]([CH3:44])[C:14]1[CH:15]=[CH:16][C:17]([CH2:20][N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[CH:18][CH:19]=1)=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 667016982,4-Bis-benzyloxy-5-isopropenyl-N-(4-morpholin-4-ylmethyl-phenyl)-benzamide

Product 1

HCID 59382273HCID 59382273, compoundYield 118.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,4-Bis-benzyloxy-5-isopropenyl-N-(4-morpholin-4-ylmethyl-phenyl)-benzamide (0.1 g, 0.18 mmol) [Method A2 from (2,4-bis-benzyloxy-5-isopropenyl)-benzoic acid (Preparation B5) and 4-morpholin-4-yl-methyl-phenylamine] were dissolved in DMF (1 ml) and treated with 60% NaH in mineral oil (11 mg, 1.6 eq) and the reaction mixture was stirred for 15 minutes followed by the addition of methyl iodide (26 mg, 0.18 mmol). The reaction mixture was then stirred for 1 hour at room temperature, and subsequently diluted with EtOAc and water. The organic phase was separated, washed with brine, dried (MgSO4), filtered and evaporated to afford the title compound as a solid (0.12 g). MS: [M+H]+ 563

Workup

  1. stirringThe reaction mixture was then stirred for 1 hour at room temperature
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-b6bccc97139c42109a91d808173915bc
Source dataset
uspto-grants-2012_01
Patent number
US08106057B2

Reaction notes

Loading…