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Potassium Carbonate → 3-{2-[5-(4-Fluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-phenoxymethyl}-benzamide

HRID 1046940
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HRID 1046940 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[OH:19])[N:10]([C:20]([C:22]3[C:27]([F:28])=[CH:26][C:25]([F:29])=[CH:24][C:23]=3[F:30])=[O:21])[N:9]=2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:38][C:39]1[CH:40]=[C:41]([CH:45]=[CH:46][CH:47]=1)[C:42]([NH2:44])=[O:43]>C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][CH:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH2:38][C:39]3[CH:40]=[C:41]([CH:45]=[CH:46][CH:47]=3)[C:42]([NH2:44])=[O:43])[N:10]([C:20](=[O:21])[C:22]3[C:27]([F:28])=[CH:26][C:25]([F:29])=[CH:24][C:23]=3[F:30])[N:9]=2)=[CH:4][CH:3]=1
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 5840703-(Bromomethyl)benzamideHCID 67279311[5-(4-Fluoro-phenyl)-2-(2-hydroxy-phenyl)-[1,3,4]thiadiazol-3-yl]-(2,4,6-trifluoro-phenyl)-methanone

생성물 1

HCID 580257043-{2-[5-(4-Fluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-phenoxymethyl}-benzamide

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

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온도
90 °C

실험 절차

To [5-(4-fluoro-phenyl)-2-(2-hydroxy-phenyl)-[1,3,4]thiadiazol-3-yl]-(2,4,6-trifluoro-phenyl)-methanone (41 μmol) dissolved in acetonitrile (1 mL) is added K2CO3 (61.5 μmol) and 3-bromomethyl-benzamide (94.2 μmol) and the mixture is heated at 90° C. After 12 hours, the reaction is complete as determined by LC/MS. Purification is accomplished by preparative LC/MS (20-100% MeCN/H2O) to give 3-{2-[5-(4-fluoro-phenyl)-3-(2,4,6-trifluoro-benzoyl)-2,3-dihydro-[1,3,4]thiadiazol-2-yl]-phenoxymethyl}-benzamide: 1H NMR (400 MHz, CDCl3) δ 8.09 (s, 1H), 7.9 (d, J=7.6 Hz, 1H), 7.7 (s, 1H), 7.6-7.5 (m, 4H) 7.35 (d, J=7.6 Hz, 1H), 7.06 (t, J=8.4 Hz, 1H), 6.99 (t, J=7.6 Hz, 2H), 6.88 (d, J=8 Hz), 6.79 (t, J=8.4 Hz, 2H), 6.26 (bs, 1H), 5.33 (d, J=7.6 Hz); LC/MS (ES+): 566.1 (M+1)+.

후처리

  1. customPurification

출처 및 근거

ORD 기록
ord-2157e974633145ccb5c6d9c3e48b8084
출처 데이터셋
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08569345B2

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