Benzyl Bromide → 2-chloro-5,11-dihydro-11-ethyl-5-methyl-8-phenylmethoxy-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 724969Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:21])[C:7](=[O:20])[C:8]3[CH:18]=[C:17]([OH:19])[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1.[H-].[Na+].[CH2:24](Br)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:21])[C:7](=[O:20])[C:8]3[CH:18]=[C:17]([O:19][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

The 2-chloro-5,11-dihydro-11-ethyl-8-hydroxy-5-methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.052 g, 0.17 mmol) was dissolved in tetrahydrofuran and treated with excess sodium hydride (60% wt.) followed by benzyl bromide (0.04 mL, 0.34 mmol). After 24 hours stirring the mixture was cooled to 0° C. and the excess sodium hydride was quenched by the dropwise addition of water and the resulting solution was extracted with dichloromethane (3×20 mL) The combined organics were dried over magnesium sulfate, concentrated and the residue was purified by chromatography (hexanes to 1:1 hexanes/ethyl acetate gradient) followed by crystallization from hexanes to give the title compound (0.035 g, 52%), m.p. 159°-160° C.

Workup

customthe excess sodium hydride was quenched by the dropwise addition of water
extractionthe resulting solution was extracted with dichloromethane (3×20 mL) The combined
dry with materialorganics were dried over magnesium sulfate
concentrationconcentrated
customthe residue was purified by chromatography (hexanes to 1:1 hexanes/ethyl acetate gradient)
customfollowed by crystallization from hexanes

Sources & evidence

ORD record: ord-136799c2b2824417a18ffd1c6cc29c72
Source dataset: uspto-grants-1998_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05705499

Reaction notes

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