3-Methoxybenzenesulfonyl chloride → 3-methoxy-N-(4-{[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]ethynyl}pyridin-2-yl)benzenesulfonamide

HRID 1253490Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1253490
[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:15]=[CH:16][C:17]=2[C:18]#[C:19][C:20]2[CH:25]=[CH:24][N:23]=[C:22]([NH2:26])[CH:21]=2)[CH:6]=[C:7]([C:9]2[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=2)[CH:8]=1.[CH3:27][O:28][C:29]1[CH:30]=[C:31]([S:35](Cl)(=[O:37])=[O:36])[CH:32]=[CH:33][CH:34]=1>N1C=CC=CC=1>[CH3:27][O:28][C:29]1[CH:30]=[C:31]([S:35]([NH:26][C:22]2[CH:21]=[C:20]([C:19]#[C:18][C:17]3[CH:16]=[N:15][N:5]4[CH:6]=[C:7]([C:9]5[CH:10]=[N:11][N:12]([CH3:14])[CH:13]=5)[CH:8]=[C:3]([O:2][CH3:1])[C:4]=34)[CH:25]=[CH:24][N:23]=2)(=[O:37])=[O:36])[CH:32]=[CH:33][CH:34]=1

Komponenten

4

Edukt 2

HCID 27375043-Methoxybenzenesulfonyl chlorideHCID 584047124-{[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]ethynyl}pyridin-2-amine

Produkt 1

HCID 673731343-methoxy-N-(4-{[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]ethynyl}pyridin-2-yl)benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of 4-{[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]ethynyl}pyridin-2-amine (24 mg, 0.070 mmol) in pyridine (1400 μl), was added 3-methoxybenzenesulfonyl chloride (29 μl, 0.203 mmol). The reaction mixture was stirred for 72 hours at room temperature. The precipitated solid was filtered and the solid washed with 10 mL of dichloromethane. The solid was dried in vacuo to afford 3-methoxy-N-(4-{[4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl]ethynyl}pyridin-2-yl)benzenesulfonamide an off-white solid. 1H NMR (500 MHz, DMSO-d6) δ 8.75 (s, 1H); 8.34 (s, 1H); 8.26 (s, 1H); 8.06 (s, 1H); 7.99 (bs, 2H); 7.49-7.42 (m, 2H); 7.38 (s, 1H); 7.16-7.15 (m, 2H); 7.11 (s, 1H); 6.85 (bs, 1H); 4.07 (s, 3H); 3.87 (s, 3H); 3.79 (s, 3H). LRMS (ESI) calculated for C26H22N6O3S [M+H]+, 515.1; found 515.1.

Aufarbeitung

  1. filtrationThe precipitated solid was filtered
  2. washthe solid washed with 10 mL of dichloromethane
  3. customThe solid was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c8e5144770bb45b3ae23332de933a2e1
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08455477B2

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