2,5-Dimethyl-3-furoyl Chloride → (S)-2,5-Dimethyl-furan-3-carboxylic acid (1-{4-[3-(4-ethoxy-phenoxy)-azetidin-1-yl]-phenyl}-ethyl)-amide

HRID 40513

Reaction equation

HRID 40513 reaction equation
[CH3:1][C:2]1[O:3][C:4]([CH3:10])=[CH:5][C:6]=1[C:7](Cl)=[O:8].[CH2:11]([O:13][C:14]1[CH:33]=[CH:32][C:17]([O:18][CH:19]2[CH2:22][N:21]([C:23]3[CH:28]=[CH:27][C:26]([C@@H:29]([NH2:31])[CH3:30])=[CH:25][CH:24]=3)[CH2:20]2)=[CH:16][CH:15]=1)[CH3:12]>C(Cl)Cl>[CH2:11]([O:13][C:14]1[CH:33]=[CH:32][C:17]([O:18][CH:19]2[CH2:20][N:21]([C:23]3[CH:28]=[CH:27][C:26]([C@@H:29]([NH:31][C:7]([C:6]4[CH:5]=[C:4]([CH3:10])[O:3][C:2]=4[CH3:1])=[O:8])[CH3:30])=[CH:25][CH:24]=3)[CH2:22]2)=[CH:16][CH:15]=1)[CH3:12]

Participants

4

Reactant 2

HCID 27348042,5-Dimethyl-3-furoyl ChlorideHCID 86689010(S)-1-{4-[3-(4-Ethoxy-phenoxy)-azetidin-1-yl]-phenyl}-ethylamine

Product 1

HCID 71616304(S)-2,5-Dimethyl-furan-3-carboxylic acid (1-{4-[3-(4-ethoxy-phenoxy)-azetidin-1-yl]-phenyl}-ethyl)-amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 0.015 g (0.10 mmol) 2,5-dimethyl-furan-3-carbonyl chloride in 1 mL DCM is added a mixture of 0.031 g (0.10 mmol) (S)-1-{4-[3-(4-ethoxy-phenoxy)-azetidin-1-yl]-phenyl}-ethylamine (X.1) and 0.010 g (0.10 mmol) TEA in 0.5 mL DCM. The mixture is stirred for 12 h at rt. The solvent is removed in vacuo and the residue is purified by HPLC to yield the desired product.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe residue is purified by HPLC

Sources & evidence

ORD record
ord-420d1ab6b86e45b88eef6d32ecab79ba
Source dataset
uspto-grants-2013_09
Patent number
US08530461B2

Linked notes

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