Hydrochloric Acid → 5-Methyl-pyridine-2-sulfonic acid [2-[2-(methanesulfonylamino-methyl)-pyridin-4-yl]-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide

HRID 1066514

Reaktionsgleichung

Reaktionsgleichung von HRID 1066514
Cl.[NH2:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[N:15]=[C:14]([NH:16][S:17]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][N:21]=3)(=[O:19])=[O:18])[C:13]([O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[O:34][CH3:35])=[C:12]([O:36][CH3:37])[N:11]=2)[CH:7]=[CH:6][N:5]=1.C(N(C(C)C)C(C)C)C.[CH3:47][S:48](Cl)(=[O:50])=[O:49].Cl>C(Cl)Cl.C(Cl)Cl.CO>[CH3:47][S:48]([NH:2][CH2:3][C:4]1[CH:9]=[C:8]([C:10]2[N:15]=[C:14]([NH:16][S:17]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][N:21]=3)(=[O:19])=[O:18])[C:13]([O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[O:34][CH3:35])=[C:12]([O:36][CH3:37])[N:11]=2)[CH:7]=[CH:6][N:5]=1)(=[O:50])=[O:49]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 867569945-Methyl-pyridine-2-sulfonic acid [2-(2-aminomethyl-pyridin-4-yl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide hydrochloride2×

Produkt 1

HCID 98731685-Methyl-pyridine-2-sulfonic acid [2-[2-(methanesulfonylamino-methyl)-pyridin-4-yl]-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

A solution of 70 mg of 5-methyl-pyridine-2-sulfonic acid [2-(2-aminomethyl-pyridin-4-yl)-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide hydrochloride, product of example 30 b), in CH2Cl2 (5 ml), was treated at RT with 50 mg of N-ethyldiisopropylamine, 15 mg of methanesulfonyl chloride and then refluxed for 18 h until the reaction was complete according to TLC analysis (CH2Cl2/MeOH: 95/5). The mixture was poured into cold diluted HCl and the product extracted into CH2Cl2. The organic layer was dried over Na2SO4 and the solvent removed in vacuo. The residue was purified on a silica gel chromatography column (eluted with Me2Cl2/MeOH: 95/5). Combination of the purified fractions and evacuation in vacuo afforded 5-methyl-pyridine-2-sulfonic acid [2-[2-(methanesulfonylamino-methyl)-pyridin-4-yl]-6-methoxy-5-(2-methoxy-phenoxy)-pyrimidin-4-yl]-amide as a light yellow solid. ISN mass spectrum, m/e 585 (M−1 calculated for C25H26N6O7S2: 585).

Aufarbeitung

  1. temperaturerefluxed for 18 h until the reaction
  2. extractionthe product extracted into CH2Cl2
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customthe solvent removed in vacuo
  5. customThe residue was purified on a silica gel chromatography column (eluted with Me2Cl2/MeOH: 95/5)

Quellen und Nachweise

ORD-Eintrag
ord-f0cf356545c246608b4f52ab7e87db66
Quelldatensatz
uspto-grants-2001_06
Patentnummer
US06242601B1

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