1-Propanesulfonyl chloride → Methyl 4-{5-[3-[(propylsulfonyl)amino]-4-(2-methylpiperidin-1-yl)phenyl]-1,2,4-oxadiazol-3-yl}-2-fluorobenzoate

HRID 219949Notes

Reaction equation

HRID 219949 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[C:22]([F:30])[CH:21]=3)[N:16]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH3:14].[CH2:31]([S:34](Cl)(=[O:36])=[O:35])[CH2:32][CH3:33]>CCOC(C)=O>[CH2:31]([S:34]([NH:1][C:2]1[CH:3]=[C:4]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[C:22]([F:30])[CH:21]=3)[N:16]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH3:14])(=[O:36])=[O:35])[CH2:32][CH3:33]

Participants

4

Reactant 2

HCID 662791-Propanesulfonyl chlorideHCID 67528581Methyl 4-{5-[3-amino-4-(2-methylpiperidin-1-yl)phenyl]-1,2,4-oxadiazol-3-yl}-2-fluorobenzoate

Product 1

HCID 67529191Methyl 4-{5-[3-[(propylsulfonyl)amino]-4-(2-methylpiperidin-1-yl)phenyl]-1,2,4-oxadiazol-3-yl}-2-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The title compound was obtained following procedure and work up described for example 67, step 1, but starting from methyl 4-{5-[3-amino-4-(2-methylpiperidin-1-yl)phenyl]-1,2,4-oxadiazol-3-yl}-2-fluorobenzoate, prepared as in example 67, Steps 1 and 2, (200 mg; 0.49 mmol) and 1-propanesulfonyl chloride (280 mg; 2 mmol). The title compound was obtained as a yellow powder after column chromatography (EtOAc:cHex from 10:90 to 100:0). LC/MS (Method B): 517.4 (M+H)+. HPLC (Method A) Rt. 6.37 min (purity: 96.5%).

Sources & evidence

ORD record
ord-49cc4683606d45ed8e895d3cf47bf8f9
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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