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Ethylene Glycol → 5-Chloro-N-((1-(4-(4-methyl-1,4-diazepan-1-yl)phenyl)-1H-pyrazol-4-yl)methyl)thiophene-2-carboxamide

HRID 643032
Notes
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Reaction equation

HRID 643032 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[CH:12]=[N:13][N:14]([C:16]3[CH:21]=[CH:20][C:19](I)=[CH:18][CH:17]=3)[CH:15]=2)=[O:8])=[CH:4][CH:3]=1.[CH3:23][N:24]1[CH2:30][CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.C(O)CO.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C(O)(C)C.[Cu]I>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[CH:12]=[N:13][N:14]([C:16]3[CH:21]=[CH:20][C:19]([N:27]4[CH2:28][CH2:29][CH2:30][N:24]([CH3:23])[CH2:25][CH2:26]4)=[CH:18][CH:17]=3)[CH:15]=2)=[O:8])=[CH:4][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 174Ethylene GlycolHCID 62657Potassium Phosphate, TribasicHCID 2283491-MethylhomopiperazineHCID 685109935-chloro-N-((1-(4-iodophenyl)-1H-pyrazol-4-yl)methyl)thiophene-2-carboxamide

Product 1

HCID 592600965-Chloro-N-((1-(4-(4-methyl-1,4-diazepan-1-yl)phenyl)-1H-pyrazol-4-yl)methyl)thiophene-2-carboxamideYield 5.2%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3776IsopropanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 5-chloro-N-((1-(4-iodophenyl)-1H-pyrazol-4-yl)methyl)thiophene-2-carboxamide (100 mg, 0.225 mmol), 1-methylhomopiperazine (0.100 mL, 0.81 mmol), ethylene glycol (0.025 mL, 0.45 mmol) and K3PO4 (100 mg, 0.47 mmol) in isopropanol (1 mL) was degassed with Argon before being charged with CuI (20 mg, 0.11 mmol). The mixture in a sealed tube was heated at 85° C. overnight. It was then purified by HPLC to give the title compound (5 mg). MS 430.0 and 432.0 (M+H, Cl pattern).

Workup

  1. customwas degassed with Argon
  2. customIt was then purified by HPLC

Sources & evidence

ORD record
ord-349fcdd75512491688e12c4a6f3b7425
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07696352B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes