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

HRID 1846935Notes

Reaction equation

HRID 1846935 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

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 66849890N-(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-8940039235a54f61ac7c010ed33dacd2
Source dataset
uspto-grants-2015_02
Patent number
US08952034B2

Reaction notes

Loading…