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4-(4-Chlorobenzoyl)-1-[4-(2,5-dihydro-1h-pyrrol-1-ylcarbonyl)benzyl]-6-methoxy-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-on → 4-(4-chlorobenzoyl)-1-[4-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benzyl]-6-hydroxy-1,3,4,5-tetrahydrobenzo[e][1,4]-diazepin-2-on

HRID 2417512
Notes
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Reaction equation

HRID 2417512 reaction equation
[Cl:1][C:2]1[CH:37]=[CH:36][C:5]([C:6]([N:8]2[CH2:14][C:13]3[C:15]([O:19]C)=[CH:16][CH:17]=[CH:18][C:12]=3[N:11]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([N:30]4[CH2:34][CH:33]=[CH:32][CH2:31]4)=[O:29])=[CH:24][CH:23]=3)[C:10](=[O:35])[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[Br-].[Br-].[Br-].B>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([N:8]2[CH2:14][C:13]3[C:15]([OH:19])=[CH:16][CH:17]=[CH:18][C:12]=3[N:11]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([N:30]4[CH2:31][CH:32]=[CH:33][CH2:34]4)=[O:29])=[CH:24][CH:23]=3)[C:10](=[O:35])[CH2:9]2)=[O:7])=[CH:36][CH:37]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 226324534-(4-Chlorobenzoyl)-1-[4-(2,5-dihydro-1h-pyrrol-1-ylcarbonyl)benzyl]-6-methoxy-1,3,4,5-tetrahydrobenzo[e][1,4]diazepin-2-onHCID 178419136HCID 178419136, compound

Product 1

HCID 226323854-(4-chlorobenzoyl)-1-[4-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benzyl]-6-hydroxy-1,3,4,5-tetrahydrobenzo[e][1,4]-diazepin-2-on

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

75 mg (0.15 mmol) of 4-(4-chlorobenzoyl)-1-[4-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benzyl]-6-methoxy-1,3,4,5-tetrahydrobenzo[e][1,4]-diazepin-2-on was dissolved in 10 ml of dichloromethane. 1.3 ml of borane tribromide was added to the obtained solution, and they were stirred at room temperature overnight. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the obtained crude product was treated in the same manner as in step 3 in Example 1 to obtain the title compound.

Workup

  1. additionwas treated in the same manner as in step 3 in Example 1

Sources & evidence

ORD record
ord-8da6a500bc2b457da6446152d01ea80e
Source dataset
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06825191B2

Reaction notes

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