Dichloromethane → HCID 131733089, compound

HRID 1518998Notes

Reaction equation

HRID 1518998 reaction equation
Cl[C:2]1[CH:13]=[CH:12][C:5]([C:6]([NH:8][CH:9]([CH3:11])[CH3:10])=[O:7])=[C:4]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[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.[Cl:41]CCl>O>[Cl:41][C:19]1[CH:20]=[CH:21][C:16]([CH2:15][N:14]([C:4]2[CH:3]=[CH:2][CH:13]=[CH:12][C:5]=2[C:6]([NH:8][CH:9]([CH3:11])[CH3:10])=[O:7])[S:37]([C:36]2[N:32]([CH3:31])[N:33]=[CH:34][CH:35]=2)(=[O:39])=[O:38])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 81531DiisopropylethylamineHCID 224726211-Methyl-1H-pyrazole-5-sulfonyl chlorideHCID 131733090HCID 131733090, compound

Product 1

HCID 131733089HCID 131733089, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 44 (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-b3110d3a783e46479a3502e47ca751a4
Source dataset
uspto-grants-2015_07
Patent number
US09073834B2

Reaction notes

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