5-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carbonyl chloride → ((S)-3-Dimethylaminomethyl-piperidin-1-yl)-[5-(4-methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophen-2-yl]-methanone

HRID 572318Notes

Reaction equation

HRID 572318 reaction equation
Cl.Cl.[CH3:3][N:4]([CH3:12])[CH2:5][C@@H:6]1[CH2:11][CH2:10][CH2:9][NH:8][CH2:7]1.[F:13][C:14]([F:30])([F:29])[C:15]1[O:19][N:18]=[C:17]([C:20]2[S:24][C:23]([C:25](Cl)=[O:26])=[CH:22][CH:21]=2)[C:16]=1[CH3:28]>>[CH3:3][N:4]([CH2:5][C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([C:25]([C:23]2[S:24][C:20]([C:17]3[C:16]([CH3:28])=[C:15]([C:14]([F:29])([F:30])[F:13])[O:19][N:18]=3)=[CH:21][CH:22]=2)=[O:26])[CH2:7]1)[CH3:12]

Participants

3

Reactant 2

HCID 866283515-(4-Methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophene-2-carbonyl chlorideHCID 129319935N,N-dimethyl-1-[(3R)-3-piperidyl]methanamine;dihydrochloride

Product 1

HCID 25212016((S)-3-Dimethylaminomethyl-piperidin-1-yl)-[5-(4-methyl-5-trifluoromethyl-isoxazol-3-yl)-thiophen-2-yl]-methanone

Procedure

Prepared from dimethyl-(R)-1-piperidin-3-ylmethyl-amine, dihydrochloride (Preparative Example 28, 108 mg, 0.5 mmol) and 5-(5-Trifluoromethyl-4-methyl-isoxazol-3-yl)-thiophene-2-carbonyl chloride (74 mg, 0.25 mmol, as prepared in Example 2 Method B) as described for the R isomer (Example 70). Colorless solid (41 mg, 41%). LC/MS 5.28 min, [M+1]+ 402.

Workup

  1. customLC/MS 5.28 min, [M+1]+ 402

Sources & evidence

ORD record
ord-145f50df970743428ac6ea048f603aba
Source dataset
uspto-grants-2015_05
Patent number
US09029397B2

Reaction notes

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