(Z)-7-Chloro-5-(4-(4-methoxybenzyloxy)phenyl)-1-methyl-3-(4-(trifluoromethyl)benzyl)-1H-benzo[e][1,4]diazepin-2(3H)-one → (Z)-7-Chloro-5-(4-hydroxyphenyl)-1-methyl-3-(4-(trifluoromethyl)benzyl)-1H-benzo[e][1,4]diazepin-2(3H)-one

HRID 885019Notes

Reaction equation

HRID 885019 reaction equation
[Cl:1][C:2]1[CH:41]=[CH:40][C:5]2[N:6]([CH3:39])[C:7](=[O:38])[CH:8]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17]CC4C=CC(OC)=CC=4)=[CH:13][CH:12]=3)[C:4]=2[CH:3]=1>Cl.O1CCOCC1>[Cl:1][C:2]1[CH:41]=[CH:40][C:5]2[N:6]([CH3:39])[C:7](=[O:38])[CH:8]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=3)[N:9]=[C:10]([C:11]3[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=3)[C:4]=2[CH:3]=1

Participants

4

Reactant 1

HCID 59594382(Z)-7-Chloro-5-(4-(4-methoxybenzyloxy)phenyl)-1-methyl-3-(4-(trifluoromethyl)benzyl)-1H-benzo[e][1,4]diazepin-2(3H)-one

Product 1

HCID 135869725(Z)-7-Chloro-5-(4-hydroxyphenyl)-1-methyl-3-(4-(trifluoromethyl)benzyl)-1H-benzo[e][1,4]diazepin-2(3H)-one

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Procedure

(Z)-7-chloro-5-(4-(4-methoxybenzyloxy)phenyl)-1-methyl-3-(4-(trifluoromethyl)benzyl)-1H-benzo[e][1,4]diazepin-2(3H)-one (50 mg, 0.086 mmol) was dissolved in 4 N HCl in dioxane (3 mL) and stirred for 3 h. The solution was then concentrated, and sonicated in 5 mL of diethyl ether. The product was collected by filtration as a bright yellow solid (24.2 mg, 61%). 1H NMR (300 MHz, DMSO-d6) δ 3.30 (s, 3H), 3.32-3.43 (m, 3H), 6.80 (d, 2H), 7.22 (d, 1H), 7.30-7.40 (m, 2H), 7.50-7.78 (m, 6H); ESI m/z measured 459.1078 [M+H+], calculated 459.1087.

Workup

  1. concentrationThe solution was then concentrated
  2. customsonicated in 5 mL of diethyl ether
  3. filtrationThe product was collected by filtration as a bright yellow solid (24.2 mg, 61%)

Sources & evidence

ORD record
ord-5b825528779c4a14afb87b4fccf8a26d
Source dataset
uspto-grants-2012_08
Patent number
US08242109B2

Reaction notes

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