1-(ethoxymethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → 3-Cyano-N-(2,4-dimethoxybenzyl)-4-{2-[1-(ethoxymethyl)-1H-pyrazol-5-yl]-4-(trifluoromethoxy)phenoxy}-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

HRID 46339

Reaktionsgleichung

Reaktionsgleichung von HRID 46339
[CH2:1]([O:3][CH2:4][N:5]1[C:9](B2OC(C)(C)C(C)(C)O2)=[CH:8][CH:7]=[N:6]1)[CH3:2].[C:19]([C:21]1[CH:22]=[C:23]([S:40]([N:43]([CH2:49][C:50]2[CH:55]=[CH:54][C:53]([O:56][CH3:57])=[CH:52][C:51]=2[O:58][CH3:59])[C:44]2[S:48][N:47]=[CH:46][N:45]=2)(=[O:42])=[O:41])[CH:24]=[CH:25][C:26]=1[O:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][C:35]([F:38])([F:37])[F:36])=[CH:30][C:29]=1I)#[N:20]>>[C:19]([C:21]1[CH:22]=[C:23]([S:40]([N:43]([CH2:49][C:50]2[CH:55]=[CH:54][C:53]([O:56][CH3:57])=[CH:52][C:51]=2[O:58][CH3:59])[C:44]2[S:48][N:47]=[CH:46][N:45]=2)(=[O:42])=[O:41])[CH:24]=[CH:25][C:26]=1[O:27][C:28]1[CH:29]=[CH:30][C:31]([O:34][C:35]([F:37])([F:36])[F:38])=[CH:32][C:33]=1[C:9]1[N:5]([CH2:4][O:3][CH2:1][CH3:2])[N:6]=[CH:7][CH:8]=1)#[N:20]

Komponenten

3

Edukt 2

HCID 594366031-(ethoxymethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 669057953-cyano-N-(2,4-dimethoxybenzyl)-4-[2-iodo-4-(trifluoromethoxy)phenoxy]-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

Produkt 1

HCID 594365673-Cyano-N-(2,4-dimethoxybenzyl)-4-{2-[1-(ethoxymethyl)-1H-pyrazol-5-yl]-4-(trifluoromethoxy)phenoxy}-N-1,2,4-thiadiazol-5-ylbenzenesulfonamideAusbeute 29 %

Versuchsvorschrift

Prepared according to Method U (below) using 1-(ethoxymethyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (Preparation 337, 197 mg, 0.714 mmol), and 3-cyano-N-(2,4-dimethoxybenzyl)-4-[2-iodo-4-(trifluoromethoxy)phenoxy]-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide (Preparation 497, 210 mg, 0.42 mmol). The material was purified by column chromatography eluting with ethyl acetate:heptane (1:1, by volume) to furnish the title compound as a white solid, 70 mg, 29% yield.

Aufarbeitung

  1. customPrepared
  2. customThe material was purified by column chromatography
  3. washeluting with ethyl acetate:heptane (1:1, by volume)

Quellen und Nachweise

ORD-Eintrag
ord-b16f8dcf08a14f53aa58919d4aff6745
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541588B2

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