Methyl iodide → HCID 67699241, compound

HRID 343194Notes

Reaction equation

HRID 343194 reaction equation
[H-].[Na+].[CH:3]([N:6]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:7](=[O:38])[CH2:8][N:9]1[C:15](=[O:16])[C:14]([CH3:26])([CH2:17][C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:19])[C:13](=[O:27])[N:12]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:11]2[CH:34]=[CH:35][CH:36]=[CH:37][C:10]1=2)([CH3:5])[CH3:4].I[CH3:46]>CN(C=O)C.Cl>[CH:3]([N:6]([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[C:7](=[O:38])[CH2:8][N:9]1[C:15](=[O:16])[C:14]([CH3:26])([CH:17]([CH3:46])[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:19])[C:13](=[O:27])[N:12]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:11]2[CH:34]=[CH:35][CH:36]=[CH:37][C:10]1=2)([CH3:5])[CH3:4]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67699881HCID 67699881, compound

Product 1

HCID 67699241HCID 67699241, compoundYield 21.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

8.2 mg (0.21 mmol) of 60% sodium hydride is added to a solution of 0.075 g (0.14 mmol) of N-Isopropyl-2-[3-methyl-2,4-dioxo-3-(2-phenyl-2-oxoethyl)-5-phenyl-2,3,4,5-tetrahydro-benzo[b][1,4]diazepin-1-yl]-N-phenyl acetamide, prepared as in Example 7, in 2 ml of DMF. After 5 min, 0.009 mL (0.15 mmol) of iodomethane is added and the solution stirred at RT for 25 min. The reaction mixture is diluted with 10 mL of 1N HCl and extracted with EtOAc (×3). The organic extracts are washed with H2O and brine, dried over MgSO4 and concentrated in vacuo to a bright yellow oil. Purification by reverse phase C-18 MPLC (70-75% methanol/H2O) gave 17 mg of the title compound as a white powder: 1H NMR (CDCl3 300 MHz) δ8.04 (d, 2H, J=7), 7.6-6.9 (m, 17H), 5.03 (m, 0.5H), 4.92 (m, 0.5H), 4.8-3.9 (m, 3H), 1.26 (dd, 3H, J=7,11), 1.12 (dd, 3H, J=2,7), 0.98 (t, 3H, J=7); low resolution MS (FAB) m/e 560 (MH+).

Workup

  1. extractionextracted with EtOAc (×3)
  2. washThe organic extracts are washed with H2O and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo to a bright yellow oil
  5. customPurification by reverse phase C-18 MPLC (70-75% methanol/H2O)

Sources & evidence

ORD record
ord-7df6f12009d941e78f0f37c2bbd5ae8b
Source dataset
uspto-grants-1999_01
Patent number
US05859007

Reaction notes

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