Diisopropylamine → HCID 66823106, compound

HRID 591208

Reaction equation

HRID 591208 reaction equation
[CH2:1]([C:8]1([C:12]2[CH:13]=[C:14]([CH:28]=[CH:29][CH:30]=2)[O:15][CH2:16][CH2:17][NH:18][S:19]([C:22]2[N:23]=[CH:24][N:25]([CH3:27])[CH:26]=2)(=[O:21])=[O:20])[CH2:11][NH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(NC(C)C)(C)C.[F:38][CH2:39][C:40](Cl)=[O:41]>ClCCl>[CH2:1]([C:8]1([C:12]2[CH:13]=[C:14]([CH:28]=[CH:29][CH:30]=2)[O:15][CH2:16][CH2:17][NH:18][S:19]([C:22]2[N:23]=[CH:24][N:25]([CH3:27])[CH:26]=2)(=[O:21])=[O:20])[CH2:11][N:10]([C:40](=[O:41])[CH2:39][F:38])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 9663Fluoroacetyl chlorideHCID 56835964N-(2-(3-(3-benzylazetidin-3-yl)phenoxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide

Product 1

HCID 66823106HCID 66823106, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-(2-(3-(3-benzylazetidin-3-yl)phenoxy)ethyl)-1-methyl-1H-imidazole-4-sulfonamide (81 mg, 0.190 mmol) in dry dichloromethane (1.5 ml) containing diisopropylamine (0,066 ml, 0,380 mmol) under argon was added fluoroacetyl chloride (0.022 ml, 0.285 mmol) and stirred at room temperature for 1 h. Washed with 1N HCl, sodium bicarbonate and brine, dried over MgSO4, filtered, evaporated and the crude material was purified by flash silica gel chromatography on 4 g SiO2-cartridge using 5% MeOH in dichloromethane affording 68.7 mg of a white solid.

Workup

  1. washWashed with 1N HCl, sodium bicarbonate and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customthe crude material was purified by flash silica gel chromatography on 4 g SiO2-cartridge

Sources & evidence

ORD record
ord-42b10022568a413a89060257eb8e5e57
Source dataset
uspto-grants-2016_01
Patent number
US09238619B2

Linked notes

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