Diethyl Ether → HCID 67658523, compound

HRID 1456642Notes

Reaction equation

HRID 1456642 reaction equation
[H-].[Na+].[C:3]([C:10]1([NH2:37])[N:16]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]2[CH:23]=[CH:24][CH:25]=[CH:26][C:13]=2[N:12]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]#[N:34])[C:28]=2[CH3:35])[C:11]1=[O:36])([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].CI.[CH3:40]COCC>C1COCC1.CCOC(C)=O.CCCCCC>[C:3]([C:10]1([NH:37][CH3:40])[N:16]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:14]2[CH:23]=[CH:24][CH:25]=[CH:26][C:13]=2[N:12]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]#[N:34])[C:28]=2[CH3:35])[C:11]1=[O:36])([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67658796HCID 67658796, compound

Product 1

HCID 67658523HCID 67658523, compoundYield 71.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

N-methylation was accomplished via dropwise addition of NaH (0.24 g, 6 mmol, THF) to a solution of the above product, Boc-3-amino-1-(methyl-3-cyanophenyl)-1,3-dihydro-5-phenyl-1,4-benzodiazapin-2-one (1.28 g, 2.74 mmol), in THF (20 ml) containing CH3I (0.65 ml, 10.4 mmol) at 0° C. for 8 hr. After dilution with Et2O and aqueous workup, concentration of the organic phase and flash chromatography (silica gel, 35% EtOAc/hexane) yielded the product, Boc-3-methylamino-1-(methyl-3-cyanophenyl)-1,3-dihydro-5-phenyl-1,4-benzodiazapin-2-one (0.94 g, 71.5 %). 1H NMR, 13C NMR, and mass analysis were consistent with structure.

Sources & evidence

ORD record
ord-95b181c830844186a4b4c1d98c4313c2
Source dataset
uspto-grants-1998_12
Patent number
US05843941

Reaction notes

Loading…