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

HRID 62825Notes

Reaction equation

HRID 62825 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 20.1%

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 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 (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-16302cba723448dc8d70b425b60aca42
Source dataset
uspto-grants-2016_09
Patent number
US09447033B2

Reaction notes

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