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(4-Chlorophenyl)acetic acid → N-(4-(6-(2-(2-(4-chlorophenyl)acetyl)hydrazinyl)pyridazin-3-yl)phenyl)methanesulfonamide

HRID 2205729
Notes
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Reaction equation

HRID 2205729 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.[NH:34]([C:36]1[N:41]=[N:40][C:39]([C:42]2[CH:47]=[CH:46][C:45]([NH:48][S:49]([CH3:52])(=[O:51])=[O:50])=[CH:44][CH:43]=2)=[CH:38][CH:37]=1)[NH2:35].C(N(C(C)C)CC)(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([NH:35][NH:34][C:36]2[N:41]=[N:40][C:39]([C:42]3[CH:43]=[CH:44][C:45]([NH:48][S:49]([CH3:52])(=[O:51])=[O:50])=[CH:46][CH:47]=3)=[CH:38][CH:37]=2)=[O:11])=[CH:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 15880(4-Chlorophenyl)acetic acidHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66849307N-(4-(6-hydrazinylpyridazin-3-yl)phenyl)methanesulfonamide

Product 1

HCID 66849890
N-(4-(6-(2-(2-(4-chlorophenyl)acetyl)hydrazinyl)pyridazin-3-yl)phenyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 2-(4-chlorophenyl)acetic acid (1.07 mmole), HOBT (1.07 mmole), and EDCI hydrochloride (1.61 mmole) in DMF (7 mL) were added N-(4-(6-hydrazinylpyridazin-3-yl)phenyl)methanesulfonamide (1.07 mmole) in 10 mL of DMF followed by diisopropylethylamine (3.77 mmole). The resulting mixture was stirred at room temperature for 22 hours and evaporated in vacuo. The desired product N-(4-(6-(2-(2-(4-chlorophenyl)acetyl)hydrazinyl)pyridazin-3-yl)phenyl)methanesulfonamide was precipitated out from water.

Workup

  1. customevaporated in vacuo
  2. customThe desired product N-(4-(6-(2-(2-(4-chlorophenyl)acetyl)hydrazinyl)pyridazin-3-yl)phenyl)methanesulfonamide was precipitated out from water

Sources & evidence

ORD record
ord-fc9abdac9c2647a48dbc59a1322b4e81
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09371329B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes