Formic Acid → 4-t-butyl-N-[2-(4-formylpiperazinyl)-6-(3-hydroxypropyloxy)-5-(2-methoxyphenoxy)-4-pyrimidinyl]benzenesulfonamide

HRID 1418346Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1418346
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])=[C:19]([O:30][CH2:31][CH2:32][CH2:33][OH:34])[N:18]=[C:17]([N:35]3[CH2:40][CH2:39][NH:38][CH2:37][CH2:36]3)[N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CCN=C=NCCCN(C)C.Cl.ON1C2C=CC=CC=2N=N1.[CH:63](O)=[O:64].Cl>CN(C)C=O.C(Cl)Cl.O>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])=[C:19]([O:30][CH2:31][CH2:32][CH2:33][OH:34])[N:18]=[C:17]([N:35]3[CH2:36][CH2:37][N:38]([CH:63]=[O:64])[CH2:39][CH2:40]3)[N:16]=2)(=[O:13])=[O:12])=[CH:9][CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

8

Edukt 5

HCID 284Formic AcidHCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 700223014-t-Butyl-N-[6-(3-hydroxypropyloxy)-5-(2-methoxyphenoxy)-2-piperazinyl-4-pyrimidinyl]-benzenesulfonamide

Produkt 1

HCID 867538784-t-butyl-N-[2-(4-formylpiperazinyl)-6-(3-hydroxypropyloxy)-5-(2-methoxyphenoxy)-4-pyrimidinyl]benzenesulfonamideAusbeute 23,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 22350042dichloromethane N,N-dimethylformamideLösungsmittel

Versuchsvorschrift

4-t-Butyl-N-[6-(3-hydroxypropyloxy)-5-(2-methoxyphenoxy)-2-piperazinyl-4-pyrimidinyl]-benzenesulfonamide (80 mg; 0.14 mmol), WSC·HCl (61.6 mg; 0.28 mmol), N-hydroxybenzotriazole (75.6 mg; 0.56 mmol), and formic acid (6.5 mg; 0.15 mmol) were dissolved in dimethylformamide-methylene chloride (1:1, 1 ml). The mixture was stirred overnight at room temperature. The reaction mixture was poured into water, made acidic with hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate, and evaporated. The residue was purified by silica gel column chromatography (chloroform:methanol=15:1), to thereby obtain 20 mg (yield: 23.8%) of the title compound as a pale yellow oil.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography (chloroform:methanol=15:1)

Quellen und Nachweise

ORD-Eintrag
ord-c4e0b269fc19486bb7956b2a5b74ea19
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05883092

Notizen zur Reaktion

Wird geladen…