Water → HCID 11531856, Verbindung

HRID 1170477Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1170477
[N:1]1([C:6]2[N:11]=[C:10]([CH3:12])[CH:9]=[C:8]([CH:13]3[CH2:17][CH2:16][CH2:15][NH:14]3)[N:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[CH2:18]1[O:31][C:30]2[CH:29]=[CH:28][C:22]([CH2:23][CH2:24][N:25]=[C:26]=[O:27])=[CH:21][C:20]=2[O:19]1.C(N(CC)CC)C.O>C1COCC1>[O:31]1[C:30]2[CH:29]=[CH:28][C:22]([CH2:23][CH2:24][NH:25][C:26]([N:14]3[CH2:15][CH2:16][CH2:17][CH:13]3[C:8]3[CH:9]=[C:10]([CH3:12])[N:11]=[C:6]([N:1]4[CH:5]=[CH:4][N:3]=[CH:2]4)[N:7]=3)=[O:27])=[CH:21][C:20]=2[O:19][CH2:18]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 44186063,4-Methylenedioxyphenethyl isocyanateHCID 167502772-(1H-Imidazol-1-yl)-4-methyl-6-(pyrrolidin-2-yl)pyrimidine

Produkt 1

HCID 11531856HCID 11531856, VerbindungAusbeute 90,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 2-imidazol-1-yl-4-methyl-6-pyrrolidin-2-yl-pyrimidine (21.8 mg, 0.095 mmol), 3,4-methylenedioxyphenethyl isocyanate (29 mg, 0.151 mmol) and triethylamine (0.4 mL) in anhydrous THF (1.5 mL) was reacted for 10 min. Water was added and the solution was extracted with ethyl acetate (2×3 mL), washed with brine and dried over Na2SO4. Evaporation of the solvent and purification by TLC plate gave 36 mg (90%) of 2-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-pyrrolidine-1-carboxylic acid (2-benzo[1,3]dioxol-5-yl-ethyl)-amide as a white solid. [M+H]+ 421.15; 1H-NMR (400 MHz, CD3OD) δ 8.65 (s, 1H), 7.99 (s, 1H), 7.14 (s, 1H), 7.11 (s, 1H), 6.65 (m, 3H), 5.88 (s, 2H), 4.98 (m, 1H), 3.62 (m, 1H), 3.55 (m, 1H), 3.34 (m, 2H), 2.69 (m, 2H), 2.56 (s, 3H), 2.41 (m, 1H), 2.03 (m, 3H); 13C-NMR (100 MHz, CD3OD) δ 173.9, 170.3, 166.5, 157.7, 147.6, 145.9, 133.2, 128.9, 121.3, 115.0, 108.6, 107.6, 106.9, 61.4, 46.4, 41.8, 35.7, 32.4, 23.3, 22.8.

Aufarbeitung

  1. extractionthe solution was extracted with ethyl acetate (2×3 mL)
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. customEvaporation of the solvent and purification by TLC plate

Quellen und Nachweise

ORD-Eintrag
ord-c0ae83d388e944788c5915fbaf138fbf
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07825256B2

Notizen zur Reaktion

Wird geladen…