Propylamine → HCID 67466578, compound

HRID 2171117Notes

Reaction equation

HRID 2171117 reaction equation
[Br:1][C:2]1[C:7]([O:8][CH2:9][C:10]([OH:12])=O)=[C:6]([O:13][CH3:14])[C:5]([O:15][CH:16]([F:18])[F:17])=[CH:4][CH:3]=1.C(N(CC)CC)C.CCN=C=[N:30][CH2:31][CH2:32][CH2:33]N(C)C.Cl.C1C=CC2N(O)N=NC=2C=1.C(N)CC>ClCCl.O>[Br:1][C:2]1[C:7]([O:8][CH2:9][C:10]([NH:30][CH2:31][CH2:32][CH3:33])=[O:12])=[C:6]([O:13][CH3:14])[C:5]([O:15][CH:16]([F:18])[F:17])=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 7852PropylamineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67461925HCID 67461925, compound

Product 1

HCID 67466578HCID 67466578, compoundYield 63.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirring solution of 2-(6-bromo-3-(difluoromethoxy)-2-methoxyphenoxy)acetic acid (420 mg, 1.284 mmol) in dichloromethane (20 mL) at 0° C. was added triethylamine (0.54 mL, 5.20 mmol), EDC.HCl (369 mg, 1.921 mmol), HOBt (393 mg, 2.56 mmol) and propylamine (227 mg, 3.85 mmol) and the reaction mixture was stirred at RT for 16 h. The reaction mixture was diluted with water and extracted with dichloromethane (3×). The combined dichloromethane layers were washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford 2-(6-Bromo-3-(difluoromethoxy)-2-methoxyphenoxy)-N-propylacetamide as a liquid (300 mg, 63%).

Workup

  1. extractionextracted with dichloromethane (3×)
  2. washThe combined dichloromethane layers were washed with brine
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cc403eb8205044d29a1a67e8bd5a4005
Source dataset
uspto-grants-2015_06
Patent number
US09051290B2

Reaction notes

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