tert-Butyl 6-(7-chloro-3-(2-chlorophenethyl)-1-(4-methoxybenzyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridine-1-carboxylate → 7-Chloro-3-(2-chlorophenethyl)-1-(4-methoxybenzyl)-5-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-6-yl)-1H-benzo[e][1,4]diazepin-2(3H)-one

HRID 1910685Notes

Reaction equation

HRID 1910685 reaction equation
[Cl:1][C:2]1[CH:48]=[CH:47][C:5]2[N:6]([CH2:38][C:39]3[CH:44]=[CH:43][C:42]([O:45][CH3:46])=[CH:41][CH:40]=3)[C:7](=[O:37])[CH:8]([CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[Cl:36])[N:9]=[C:10]([C:11]3[CH:12]=[C:13]4[N:19](C(OC(C)(C)C)=O)[C:18](=[O:27])[NH:17][C:14]4=[N:15][CH:16]=3)[C:4]=2[CH:3]=1>Cl.O1CCOCC1>[Cl:1][C:2]1[CH:48]=[CH:47][C:5]2[N:6]([CH2:38][C:39]3[CH:40]=[CH:41][C:42]([O:45][CH3:46])=[CH:43][CH:44]=3)[C:7](=[O:37])[CH:8]([CH2:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[Cl:36])[N:9]=[C:10]([C:11]3[CH:12]=[C:13]4[NH:19][C:18](=[O:27])[NH:17][C:14]4=[N:15][CH:16]=3)[C:4]=2[CH:3]=1

Participants

4

Reactant 1

HCID 67471943tert-Butyl 6-(7-chloro-3-(2-chlorophenethyl)-1-(4-methoxybenzyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridine-1-carboxylate

Product 1

HCID 672828807-Chloro-3-(2-chlorophenethyl)-1-(4-methoxybenzyl)-5-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-6-yl)-1H-benzo[e][1,4]diazepin-2(3H)-oneYield 75%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 6-(7-chloro-3-(2-chlorophenethyl)-1-(4-methoxybenzyl)-2-oxo-2,3-dihydro-1H-benzo[e][1,4]diazepin-5-yl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridine-1-carboxylate (90 mg) was dissolved in 4 N HCl in dioxane (10 mL), and stirred at room temperature for 2 h, then concentrated delivering pure product (50 mg, 75% yield). MS (ES+) m/z 607.9 (M+Na).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-4c1797871f534480b69228775a882fe5
Source dataset
uspto-grants-2013_12
Patent number
US08604023B2

Reaction notes

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