Ethyl isocyanate → 1-(2-(2-(3-(Benzyloxy)pyridin-2-ylamino)thiazol-4-yl)ethyl)-3-ethylurea

HRID 1426175Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1426175
[NH2:1][CH2:2][CH2:3][C:4]1[N:5]=[C:6]([NH:9][C:10]2[C:15]([O:16][CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:14][CH:13]=[CH:12][N:11]=2)[S:7][CH:8]=1.[N:24]([CH2:27][CH3:28])=[C:25]=[O:26]>CN(C=O)C>[CH2:17]([O:16][C:15]1[C:10]([NH:9][C:6]2[S:7][CH:8]=[C:4]([CH2:3][CH2:2][NH:1][C:25]([NH:24][CH2:27][CH3:28])=[O:26])[N:5]=2)=[N:11][CH:12]=[CH:13][CH:14]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

4

Edukt 2

HCID 8022Ethyl isocyanateHCID 866397044-(2-aminoethyl)-N-(3-(benzyloxy)pyridin-2-yl)thiazol-2-amine

Produkt 1

HCID 166616061-(2-(2-(3-(Benzyloxy)pyridin-2-ylamino)thiazol-4-yl)ethyl)-3-ethylureaAusbeute 30,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Crude 4-(2-aminoethyl)-N-(3-(benzyloxy)pyridin-2-yl)thiazol-2-amine (Example 134, Step A; 0.25 g, 0.766 mmol) was dissolved in DMF (20 mL), and isocyanatoethane (0.109 g, 1.53 mmol) was added. The reaction mixture was stirred for 2 hours, then partitioned between ethyl acetate and water. The organic layer was washed with water and brine, dried, and concentrated. The residue was purified via MPLC (Biotage) eluting with ethyl acetate to afford the title compound (0.092 g, 30.2% yield) as a light yellow powder. 1H NMR (DMSO-d6) δ 0.97 (t, 3H), 2.67 (t, 2H), 2.98 (m, 2H), 3.29 (m, 2H), 5.26 (s, 2H), 5.82 (bt, 2H), 6.64 (s, 1H), 6.88 (m, 1H), 7.32-7.43 (m, 4H), 7.58 (d, 2H), 7.85 (d, 1H), 7.95 (s, 1H), 9.91 (s, 1H).

Aufarbeitung

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed with water and brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified via MPLC (Biotage)
  6. washeluting with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-a0260233e9be47c580fdd12c9e752166
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933077B2

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