Bis(2-bromoethyl) ether → 4-[4-(3-Chloro-4-morpholin-4-ylmethyl-phenyl)-1H-pyrazol-3-yl]-1H-pyrrole-2-carboxylic acid [1-(3-chloro-4-fluoro-phenyl)-2-hydroxy-ethyl]-amide

HRID 1814151Notes

Reaction equation

HRID 1814151 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([NH:12][C:13]([C:15]2[NH:16][CH:17]=[C:18]([C:20]3[C:24]([C:25]4[CH:30]=[CH:29][C:28]([CH2:31][NH2:32])=[C:27]([Cl:33])[CH:26]=4)=[CH:23][NH:22][N:21]=3)[CH:19]=2)=[O:14])[CH2:10][OH:11])[CH:5]=[CH:6][C:7]=1[F:8].Br[CH2:35][CH2:36][O:37][CH2:38][CH2:39]Br>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([NH:12][C:13]([C:15]2[NH:16][CH:17]=[C:18]([C:20]3[C:24]([C:25]4[CH:30]=[CH:29][C:28]([CH2:31][N:32]5[CH2:39][CH2:38][O:37][CH2:36][CH2:35]5)=[C:27]([Cl:33])[CH:26]=4)=[CH:23][NH:22][N:21]=3)[CH:19]=2)=[O:14])[CH2:10][OH:11])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 21521Bis(2-bromoethyl) etherHCID 178509601HCID 178509601, compound

Product 1

HCID 1785234424-[4-(3-Chloro-4-morpholin-4-ylmethyl-phenyl)-1H-pyrazol-3-yl]-1H-pyrrole-2-carboxylic acid [1-(3-chloro-4-fluoro-phenyl)-2-hydroxy-ethyl]-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of benzyl amine 11 (0.05 mmol) in DMF (3 mL) was added TEA (0.15 mmol) and 2-bromoethyl ether (0.05 mmol). The resulting solution was stirred for 18 h at 70° C. The solvent was removed under vacuum and the crude products purified by preparatory HPLC to afford II-6 as a yellow oil.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe crude products purified by preparatory HPLC
  3. customto afford II-6 as a yellow oil

Sources & evidence

ORD record
ord-5c4968bb432141cdbedf70774a2fdce1
Source dataset
uspto-grants-2005_04
Patent number
US06875789B2

Reaction notes

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