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Succinate → (2R,3S) N1-[(3S)-1,3-dihydro-1-methyl-2-oxo-5-phenyl-2H-1,4-benzodiazepin-3-yl]-2-(2-methylpropyl)-3-(cyclopentylethyl)-butanediamide

HRID 272525
Notes
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Reaction equation

HRID 272525 reaction equation
[CH:1]1([CH2:6][CH2:7]I)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:9][N:10]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[C:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:13][CH:12]([NH:27][C:28](=[O:50])[C@H:29]([CH2:46][CH:47]([CH3:49])[CH3:48])[C@H:30](CC=C)[C:31]([NH:33]CC2C=C(F)C=C(F)C=2)=[O:32])[C:11]1=[O:51].C([O-])(=O)CCC([O-])=O.CN1C2C=CC=CC=2C(C2C=CC=CC=2)=NC(N)C1=O>>[CH3:9][N:10]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[C:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[N:13][C@H:12]([NH:27][C:28](=[O:50])[C@H:29]([CH2:46][CH:47]([CH3:49])[CH3:48])[C@H:30]([CH2:7][CH2:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)[C:31]([NH2:33])=[O:32])[C:11]1=[O:51]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 160419SuccinateHCID 27296813-Amino-1-methyl-5-phenyl-1H-benzo[E][1,4]diazepin-2(3H)-oneHCID 9916426(2R,3S)N1-[1,3-dihydro-1-methyl-2-oxo-5-phenyl-2H-1,4-benzodiazepin-3-yl]-2-(2-methylpropyl)-3-allyl-N4-[3,5-difluorobenzyl]-butanediamideHCID 22135275(2-Iodoethyl)cyclopentane

Product 1

HCID 9936373
(2R,3S) N1-[(3S)-1,3-dihydro-1-methyl-2-oxo-5-phenyl-2H-1,4-benzodiazepin-3-yl]-2-(2-methylpropyl)-3-(cyclopentylethyl)-butanediamide

Procedure

A procedure analogous to the preparation of Example 5 was followed. The appropriate succinate ester was prepared using the method disclosed in PCT publication WO 98/51665, using 2-(cyclopentyl)ethyl iodide for R3—X in place of allyl bromide (see Scheme 2). The anti-succinate half-ester was coupled to (S)-isomer benzodiazepine (30) using the procedures of Step 1. After Steps 2 and 3, the title compound was isolated. MS (M+H)+=475; (M+Na)+=497.2.

Workup

  1. customA procedure analogous to the preparation of Example 5

Sources & evidence

ORD record
ord-92d46e15150544a59dcd411a3ac40818
Source dataset
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07456172B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes