3-Chloropropanesulphonyl chloride → 3-Chloro-N-({4-[4-(3-chloro-4-fluorophenyl)-5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl]-1,2,5-oxadiaz ol-3-yl}methyl)propane-1-sulfonamide

HRID 1845779Notes

Reaction equation

[NH2:1][CH2:2][C:3]1[C:4]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[C:15]([Cl:20])[CH:14]=3)[C:11](=[O:21])[O:10][N:9]=2)=[N:5][O:6][N:7]=1.CCN(C(C)C)C(C)C.[Cl:31][CH2:32][CH2:33][CH2:34][S:35](Cl)(=[O:37])=[O:36]>C(Cl)Cl>[Cl:31][CH2:32][CH2:33][CH2:34][S:35]([NH:1][CH2:2][C:3]1[C:4]([C:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[C:15]([Cl:20])[CH:14]=3)[C:11](=[O:21])[O:10][N:9]=2)=[N:5][O:6][N:7]=1)(=[O:37])=[O:36]

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 3-[4-(aminomethyl)-1,2,5-oxadiazol-3-yl]-4-(3-chloro-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one (100 mg, 0.32 mol) in DCM (2 mL) under an atmosphere of nitrogen was added DIPEA (168 μL, 0.96 mmol), and 3-chloropropane-1-sulfonyl chloride (117 μL, 0.66 mmol). The reaction was stirred at 25° C. for 5 min. The reaction was quenched with MeOH and purified by preparative HPLC to yield the desired product (38 mg, 20%). 1H NMR (400 MHz, CDCl3): δ□ 7.5 (m, 1H), 7.3 (m, 2H), 4.8 (d, 2H), 3.7 (t, 2H), 3.25 (t, 2H), 2.3 (m, 2H). MF=C14H12Cl2FN5O5S; LCMS calculated for C14H13Cl2FN5O5S (M+H)+: m/z=452.2

Workup

customThe reaction was quenched with MeOH
custompurified by preparative HPLC

Sources & evidence

ORD record: ord-a930f7221ad34b62a88ecacc815ffa46
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08951536B2

Reaction notes

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