Triethylamine → tetrahydro-thiopyran-4-carboxylic acid N'-[2-(2-bromo-4-fluoro-phenoxy)-acetyl]-N'-isopropyl-hydrazide

HRID 2250892Notes

Reaction equation

HRID 2250892 reaction equation
[CH:1]([NH:4][NH:5][C:6]([CH:8]1[CH2:13][CH2:12][S:11][CH2:10][CH2:9]1)=[O:7])([CH3:3])[CH3:2].[Br:14][C:15]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:16]=1[O:17][CH2:18][C:19](O)=[O:20].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.C(N(CC)CC)C>CN(C=O)C>[Br:14][C:15]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:16]=1[O:17][CH2:18][C:19]([N:4]([CH:1]([CH3:3])[CH3:2])[NH:5][C:6]([CH:8]1[CH2:9][CH2:10][S:11][CH2:12][CH2:13]1)=[O:7])=[O:20]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 3028732-(2-Bromo-4-fluorophenoxy)acetic acidHCID 58689896tetrahydro-thiopyran-4-carboxylic acid N'-isopropyl-hydrazide

Product 1

HCID 58689901tetrahydro-thiopyran-4-carboxylic acid N'-[2-(2-bromo-4-fluoro-phenoxy)-acetyl]-N'-isopropyl-hydrazideYield 18.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of tetrahydro-thiopyran-4-carboxylic acid N′-isopropyl-hydrazide (300 mg, 1.48 mmol) and (2-bromo-4-fluoro-phenoxy)-acetic acid (369 mg, 1.48 mmol) in DMF (6 ml) was treated at rt with HOBT (240 mg, 1.78 mmol), EDCI (341 mg, 1.78 mmol), and triethylamine (0.620 ml, 4.45 mmol). The reaction mixture was stirred at room temperature for 18 hours and then partitioned between 1N HCl solution and ethyl acetate. The organic layer was washed with water, brine, dried over sodium sulfate, filtered and concentrated under vacuum. The crude was purified by RP HPLC to afford the product as a solid (116 mg, 18.1%).

Workup

  1. custompartitioned between 1N HCl solution and ethyl acetate
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe crude was purified by RP HPLC

Sources & evidence

ORD record
ord-8020f60e912f484987a5dc5bb902f91a
Source dataset
uspto-grants-2008_01
Patent number
US07317125B2

Reaction notes

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