Hydroxylamine → 4-((4-bromo-1-trityl-1H-imidazol-2-yl)(5-ethoxy-2-fluoro-3-isopropoxyphenyl)methylamino)-N'-hydroxybenzamidine

HRID 2104971Notes

Reaction equation

HRID 2104971 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([N:26]([CH2:35][C:36]2[CH:41]=[C:40]([O:42][CH2:43][CH3:44])[CH:39]=[C:38]([O:45][CH:46]([CH3:48])[CH3:47])[C:37]=2[F:49])[C:27]2[CH:34]=[CH:33][C:30]([C:31]#[N:32])=[CH:29][CH:28]=2)[N:5]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=1.[OH2:50].[NH2:51]O>CS(C)=O>[Br:1][C:2]1[N:3]=[C:4]([N:26]([CH2:35][C:36]2[CH:41]=[C:40]([O:42][CH2:43][CH3:44])[CH:39]=[C:38]([O:45][CH:46]([CH3:48])[CH3:47])[C:37]=2[F:49])[C:27]2[CH:28]=[CH:29][C:30]([C:31]([NH2:51])=[N:32][OH:50])=[CH:33][CH:34]=2)[N:5]([C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:6]=1

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 962WaterHCID 688128174-((4-bromo-1-trityl-1H-imidazol-2-yl)(5-ethoxy-2-fluoro-3-isopropoxyphenyl)methylamino)benzonitrile

Product 1

HCID 866079354-((4-bromo-1-trityl-1H-imidazol-2-yl)(5-ethoxy-2-fluoro-3-isopropoxyphenyl)methylamino)-N'-hydroxybenzamidine

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of Intermediate 28.1 (2.00 g, 2.8 mmol) in 3M NH2OH in DMSO (6 mL) (prepared according to example 1) was heated at 60° C. for 3 h. The reaction mixture was poured into water and the resultant precipitate was collected by filtration and dried in vacuo to afford Intermediate 66.1, which was used in the following step without purification.

Workup

  1. filtrationthe resultant precipitate was collected by filtration
  2. customdried in vacuo

Sources & evidence

ORD record
ord-04f85076da30401888a17ac344529ea9
Source dataset
uspto-grants-2009_08
Patent number
US07576098B2

Reaction notes

Loading…