2-(4-Amino-3-chloro-5-trifluoromethyl-benzyl)-4-oxo-4-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-butyraldehyde → 3-(-{4-(4-Amino-3-chloro-5-trifluoromethyl-phenyl)-3-[3-(3-pyrrolidin-1-yl-propyl)-3h-imidazo[4,5-c]pyridin-2-yl]-butyryl}-piperidin-4-yl)-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-one

HRID 494756Notes

Reaction equation

HRID 494756 reaction equation
[NH2:1][C:2]1[C:32]([C:33]([F:36])([F:35])[F:34])=[CH:31][C:5]([CH2:6][CH:7]([CH2:10][C:11](=[O:30])[N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:24][CH2:23][C:22]4[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=4[NH:20][C:19]3=[O:29])[CH2:14][CH2:13]2)[CH:8]=O)=[CH:4][C:3]=1[Cl:37].[N:38]1([CH2:43][CH2:44][CH2:45][NH:46][C:47]2[CH:48]=[N:49][CH:50]=[CH:51][C:52]=2[NH2:53])[CH2:42][CH2:41][CH2:40][CH2:39]1>>[NH2:1][C:2]1[C:32]([C:33]([F:36])([F:35])[F:34])=[CH:31][C:5]([CH2:6][CH:7]([C:8]2[N:46]([CH2:45][CH2:44][CH2:43][N:38]3[CH2:42][CH2:41][CH2:40][CH2:39]3)[C:47]3[CH:48]=[N:49][CH:50]=[CH:51][C:52]=3[N:53]=2)[CH2:10][C:11]([N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[CH2:24][CH2:23][C:22]4[CH:25]=[CH:26][CH:27]=[CH:28][C:21]=4[NH:20][C:19]3=[O:29])[CH2:14][CH2:13]2)=[O:30])=[CH:4][C:3]=1[Cl:37]

Participants

3

Reactant 2

HCID 221845352-(4-Amino-3-chloro-5-trifluoromethyl-benzyl)-4-oxo-4-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-butyraldehyde2×HCID 85865444HCID 85865444, compound2×

Product 1

HCID 221846263-(-{4-(4-Amino-3-chloro-5-trifluoromethyl-phenyl)-3-[3-(3-pyrrolidin-1-yl-propyl)-3h-imidazo[4,5-c]pyridin-2-yl]-butyryl}-piperidin-4-yl)-1,3,4,5-tetrahydro-1,3-benzodiazepin-2-oneYield 11%

Procedure

The product was prepared analogously to Example 62 starting from 2-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-4-oxo-4-[4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidin-1-yl]-butyraldehyde (Intermediate product 36) and N3-(3-pyrrolidin-1-yl-propyl)-pyridine-3,4-diamine (Intermediate product 41) at 100° C. and purified by HPLC-MS (Zorbax Bonus C18 amide-phase 5 μm, gradient 0.15% formic acid in water/acetonitrile 10/90→90/10 v/v). Lyophilisation of a 1 N aqueous solution of the product yielded the corresponding hydrochloride.

Workup

  1. custompurified by HPLC-MS (Zorbax Bonus C18 amide-phase 5 μm, gradient 0.15% formic acid in water/acetonitrile 10/90→90/10 v/v)

Sources & evidence

ORD record
ord-61a1c0df1cc346ce8ad965ac6aa0073f
Source dataset
uspto-grants-2009_05
Patent number
US07538115B2

Reaction notes

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