HCID 15819130, Verbindung → 5-isopropyl-N-[6-chloro-5-(o-methoxyphenoxy)-4-pyrimidinyl]-2-pyridine sulfonamide

HRID 2085090

Reaktionsgleichung

Reaktionsgleichung von HRID 2085090
Cl[C:2]1[C:7]([O:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[C:6]([Cl:17])[N:5]=[CH:4][N:3]=1.[K+].[CH:19]([C:22]1[CH:23]=[CH:24][C:25]([S:28]([NH-:31])(=[O:30])=[O:29])=[N:26][CH:27]=1)([CH3:21])[CH3:20]>CN(C=O)C>[CH:19]([C:22]1[CH:23]=[CH:24][C:25]([S:28]([NH:31][C:2]2[C:7]([O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][CH3:16])=[C:6]([Cl:17])[N:5]=[CH:4][N:3]=2)(=[O:30])=[O:29])=[N:26][CH:27]=1)([CH3:21])[CH3:20]

Komponenten

4

Edukt 2

HCID 15819130HCID 15819130, VerbindungHCID 1317209445-Isopropyl pyridine-2-sulfonamide potassium salt

Produkt 1

HCID 227294075-isopropyl-N-[6-chloro-5-(o-methoxyphenoxy)-4-pyrimidinyl]-2-pyridine sulfonamideAusbeute 64,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of 2.71 g of 4,6-dichloro-5-(o-methoxyphenoxy)-pyrimidine (Example 10b) and 5.0 g of 5-isopropyl pyridine-2-sulfonamide potassium salt (Example 1e) in 50 ml of DMF was stirred at room temperature for 20 h. The solvent was removed in vacuo, the residue was taken up in 200 ml of 10% aqueous acetic acid and extracted three times with ethyl acetate. The combined organic layers were washed with water and brine, dried over MgSO4 and evaporated. The crude product was crysallised from a mixture of 2-propanol and diethyl ether. The crystals were collected, washed with cold 2-propanol and diethyl ether and dried to give 2.8 g of 5-isopropyl-N-[6-chloro-5-(o-methoxyphenoxy)-4-pyrimidinyl]-2-pyridine sulfonamide as white crystals. LC-MS: tR=4.99 min, [M+1]+=435.25, [M−1]−=433.28.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. extractionextracted three times with ethyl acetate
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. additionThe crude product was crysallised from a mixture of 2-propanol and diethyl ether
  7. customThe crystals were collected
  8. washwashed with cold 2-propanol and diethyl ether
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-6dd33fb52f5a4519940194809d77d15b
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06720322B2

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