Potassium Carbonate → 10-({2'-[2-Amino-2-(hydroxyimino)ethyl]-1,1'-biphenyl-4-YL}carbonyl)-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-C][1,4]benzodiazepine-3-carboxamide

HRID 2244223Notes

Reaction equation

HRID 2244223 reaction equation
[C:1]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([N:18]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[CH2:22][N:21]3[C:29]([C:32]([NH:34][CH2:35][C:36]4[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=4)=[O:33])=[CH:30][CH:31]=[C:20]3[CH2:19]2)=[O:17])=[CH:12][CH:11]=1)#[N:2].Cl.[NH2:43][OH:44].C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[NH2:2][C:1](=[N:43][OH:44])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:11]=[CH:12][C:13]([C:16]([N:18]2[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=3[CH2:22][N:21]3[C:29]([C:32]([NH:34][CH2:35][C:36]4[CH:37]=[N:38][CH:39]=[CH:40][CH:41]=4)=[O:33])=[CH:30][CH:31]=[C:20]3[CH2:19]2)=[O:17])=[CH:14][CH:15]=1

Participants

6

Reactant 3

HCID 11430Potassium Carbonate2×HCID 443297Hydroxyamine hydrochloride2×HCID 1595170510-{[2'-(Cyanomethyl)-1,1'-biphenyl-4-yl]carbonyl}-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide

Product 1

HCID 7300557910-({2'-[2-Amino-2-(hydroxyimino)ethyl]-1,1'-biphenyl-4-YL}carbonyl)-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-C][1,4]benzodiazepine-3-carboxamideYield 22.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 0.806 g (0015 mol) of 10-{[2′-(cyanomethyl)-1,1′-biphenyl-4-yl]carbonyl}-N-(pyridin-3-ylmethyl)-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxamide of Example 17, 0.52 g (0.0075 mol) of hydroxylamine hydrochloride and 1.03 g (0.0075 mol) of potassium carbonate in 100 mL of ethanol and 25 mL of water was heated under reflux for 2 hours. An additional 1.04 g (0.015 mol) of hydroxylamine hydrochloride and 2.06 g (0.015 mol) of potassium carbonate was added to the and refluxing was allowed to continue until LC/MS indicated that all the starting nitrile was consumed. The solvents were removed in vacuo and the residue was washed with water and purified by chromatography to provide the title compound (0.191 g), m.p. 131-134° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. temperaturerefluxing
  4. customwas consumed
  5. customThe solvents were removed in vacuo
  6. washthe residue was washed with water
  7. custompurified by chromatography

Sources & evidence

ORD record
ord-8fc31517ce5d4412b9d7ca18f5b07a9c
Source dataset
uspto-grants-2010_03
Patent number
US07678787B2

Reaction notes

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