4-Methylmorpholine → 5-(4-Trifluoromethoxy-phenyl)-pent-4-ynoic acid methoxy-methyl-amide

HRID 852401Notes

Reaction equation

HRID 852401 reaction equation
[F:1][C:2]([F:18])([F:17])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][CH2:12][CH2:13][C:14]([OH:16])=O)=[CH:6][CH:5]=1.Cl.[CH3:20][NH:21][O:22][CH3:23].CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[CH3:23][O:22][N:21]([CH3:20])[C:14](=[O:16])[CH2:13][CH2:12][C:11]#[C:10][C:7]1[CH:6]=[CH:5][C:4]([O:3][C:2]([F:1])([F:18])[F:17])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 688226854-Pentynoic acid, 5-[4-(trifluoromethoxy)phenyl]-

Product 1

HCID 860870035-(4-Trifluoromethoxy-phenyl)-pent-4-ynoic acid methoxy-methyl-amideYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1.00 g (3.87 mmol) of 5-(4-trifluoromethoxy-phenyl)-pent-4-ynoic acid (example 29D]) in 50 ml CH2Cl2 was treated with 0.45 g (4.65 mmol) N,O-dimethylhydroxylamine hydrochloride, 0.55 ml (5.03 mmol) N-methylmorpholine and at 0° C. with 0.97 g (5.03 mmol) N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDCI). The reaction was naturally warmed to ambient temperature over night and partitioned between aqueous 10% KHSO4/ether (three times). The organic phases were washed with aqueous saturated NaHCO3, 10% NaCl and dried (Na2SO4) to give 1.165 g of the title compound as brown oil.

Workup

  1. custompartitioned between aqueous 10% KHSO4/ether (three times)
  2. washThe organic phases were washed with aqueous saturated NaHCO3, 10% NaCl
  3. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-00502c837f454a7482a8156a18d8c32a
Source dataset
uspto-grants-2007_08
Patent number
US07253192B2

Reaction notes

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