Diisopropylethylamine → 3-[(4-Chloro-benzyl)-(2-methyl-2H-pyrazole-3-sulfonyl)-amino]-N-isopropyl-benzamide

HRID 1186267Notes

Reaction equation

HRID 1186267 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][NH:7][C:8]2[CH:9]=[C:10]([CH:17]=[CH:18][CH:19]=2)[C:11]([NH:13][CH:14]([CH3:16])[CH3:15])=[O:12])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:31][N:32]1[C:36]([S:37](Cl)(=[O:39])=[O:38])=[CH:35][CH:34]=[N:33]1>ClCCl.O>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]([S:37]([C:36]2[N:32]([CH3:31])[N:33]=[CH:34][CH:35]=2)(=[O:39])=[O:38])[C:8]2[CH:9]=[C:10]([CH:17]=[CH:18][CH:19]=2)[C:11]([NH:13][CH:14]([CH3:16])[CH3:15])=[O:12])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 224726211-Methyl-1H-pyrazole-5-sulfonyl chlorideHCID 43693912HCID 43693912, compound

Product 1

HCID 461825513-[(4-Chloro-benzyl)-(2-methyl-2H-pyrazole-3-sulfonyl)-amino]-N-isopropyl-benzamideYield 26.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

3-(4-Chloro-benzylamino)-N-isopropyl-benzamide (30 mg, 0.1 mmol), diisopropylethylamine (35 μL, 0.2 mmol) and 1-methyl-1H-pyrazole-5-sulfonyl chloride (36 mg, 0.2 mmol) were stirred in dry dichloromethane (2 ml) at room temperature for 72 hrs. The reaction was diluted with dichloromethane (5 ml) and water (5 ml) with stirring. The organics were collected, dried (PTFE frit) and concentrated in vacuo. The residue was purified by preparative TLC (10% ethyl acetate/dichloromethane) to yield the product as an off-white solid (11.9 mg). HPLC retention time 8.04 min. Mass spectrum (ES+) m/z 447 (M+H).

Workup

  1. customThe organics were collected
  2. dry with materialdried (PTFE frit)
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by preparative TLC (10% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-55e15b7281674c09a5d690dd88eafd5c
Source dataset
uspto-grants-2014_03
Patent number
US08673901B2

Reaction notes

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