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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 1845779
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HRID 1845779 반응식
[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]
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참가 물질

5

반응물 3

HCID 154103-Chloropropanesulphonyl chlorideHCID 81531DiisopropylethylamineHCID 589418433-[4-(Aminomethyl)-1,2,5-oxadiazol-3-yl]-4-(3-chloro-4-fluorophenyl)-1,2,4-oxadiazol-5(4H)-one

생성물 1

HCID 589417833-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-sulfonamide수율 20%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

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온도
25 °C

실험 절차

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

후처리

  1. customThe reaction was quenched with MeOH
  2. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-a930f7221ad34b62a88ecacc815ffa46
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08951536B2

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