Triethylamine → HCID 69655432, compound

HRID 11641Notes

Reaction equation

HRID 11641 reaction equation
[NH2:1][CH2:2][C:3]1[CH:28]=[C:27]([Cl:29])[CH:26]=[CH:25][C:4]=1[O:5][CH2:6][C:7]([N:9]1[CH2:14][C@H:13]([CH3:15])[N:12]([CH2:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[CH2:11][C@H:10]1[CH3:24])=[O:8].C(N(CC)CC)C.CN(C1C=CC=CN=1)C.C([O:48][C:49](=[O:56])[CH:50]([S:52](Cl)(=[O:54])=[O:53])[CH3:51])C>O1CCCC1.C(OCC)(=O)C>[Cl:29][C:27]1[CH:26]=[CH:25][C:4]([O:5][CH2:6][C:7]([N:9]2[CH2:14][C@H:13]([CH3:15])[N:12]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH2:11][C@H:10]2[CH3:24])=[O:8])=[C:3]([CH:28]=1)[CH2:2][NH:1][S:52]([CH:50]([CH3:51])[C:49]([OH:56])=[O:48])(=[O:54])=[O:53]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 122251022-Chlorosulfonyl-propionic acid ethyl esterHCID 54187452(2R,5S)-2-(2-Aminomethyl-4-chloro-phenoxy)-1-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-ethanone

Product 1

HCID 69655432HCID 69655432, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(2-aminomethyl-4-chloro-phenoxy)-1-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-ethanone (0.05 g, 0.119 mmol) in tetrahydrofuran (1 ml) at −40° C. was added triethylamine (0.021 ml, 0.151 mmol), catalytic dimethylaminopyridine and finally a solution of 2-chlorosulfonyl-propionic acid ethyl ester (for preparation, see: Helv. Chim. Acta., (1997) 80, 671 and Bull. Soc. Chim. Fr. (1975), 807) (0.029 g, 0.145 mmol) in tetrahydrofuran (0.25 ml), added over 5 minutes. The reaction was allowed to warm to ambient temperature. After 23 hours the reaction was diluted with ethyl acetate and washed with pH 7 phosphate buffer (0.5 M). The organic layer was dried over magnesium sulfate, filtered and concentrated. The desired product was isolated via silica gel chromatography (0.047 g). This ester (0.07 mmol) was dissolved in 1:1 tetrahydrofuran:water (1 ml) and lithium hydroxide hydrate (5.8 mg, 0.138 mmol) was added. After 21 hours the reaction was concentrated and the title compound obtained after silica gel chromatography (0.039 g, LRMS: 556.1).

Workup

  1. washwashed with pH 7 phosphate buffer (0.5 M)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-23074664ee454d3abe3137f8c295aaf7
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Reaction notes

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