Water → Methanesulfonic Acid 3-{3-[3-(4-cyano-5-methylsulfanyl-3-pyridin-3-yl-thiophene-2-yl)-4-methyl-phenylamino]-phenoxyl}-propyl Ester

HRID 478187

Reaktionsgleichung

Reaktionsgleichung von HRID 478187
[OH:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([CH3:34])=[C:17]([C:19]3[S:23][C:22]([S:24][CH3:25])=[C:21]([C:26]#[N:27])[C:20]=3[C:28]3[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=3)[CH:18]=2)[CH:9]=[CH:10][CH:11]=1.CCN(CC)CC.[CH3:42][S:43](Cl)(=[O:45])=[O:44].O>C(Cl)Cl>[C:26]([C:21]1[C:20]([C:28]2[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=2)=[C:19]([C:17]2[CH:18]=[C:13]([NH:12][C:8]3[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=3)[O:5][CH2:4][CH2:3][CH2:2][O:1][S:43]([CH3:42])(=[O:45])=[O:44])[CH:14]=[CH:15][C:16]=2[CH3:34])[S:23][C:22]=1[S:24][CH3:25])#[N:27]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 220190305-{5-[3-(3-Hydroxy-propoxy)-phenylamino]-2-methyl-phenyl}-2-methylsulfanyl-4-pyridin-3-yl-thiophene-3-carbonitrile

Produkt 1

HCID 86588175Methanesulfonic Acid 3-{3-[3-(4-cyano-5-methylsulfanyl-3-pyridin-3-yl-thiophene-2-yl)-4-methyl-phenylamino]-phenoxyl}-propyl Ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 5-{5-[3-(3-hydroxy-propoxy)-phenylamino]-2-methyl-phenyl}-2-methylsulfanyl-4-pyridin-3-yl-thiophene-3-carbonitrile (370 mg, 0.76 mmol) in DCM (10 mL) was added Et3N (155 mg, 0.15 mmol) followed by MsCl (130 mg, 1.15 mmol). The resulting mixture was stirred at ambient temperature for 10 min under nitrogen then poured into 20 ml water and extracted with DCM (20 ml×3). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The desired product was obtained (391 mg, 91%) and confirmed by LC/MS (Calculated: 565.12; observed: 565.1+1, ES+).

Aufarbeitung

  1. extractionextracted with DCM (20 ml×3)
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-0bcad43845134d82b5e8eeed7357a43f
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642227B2

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