Benzeneethanamine, alpha-methyl-, phosphate (1:1) → (S)-2'-(2-fluoropyridin-3-yl)-7'-(3-methylisoxazol-5-yl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

HRID 335784

Reaktionsgleichung

Reaktionsgleichung von HRID 335784
Br[C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([C:16]4[C:17]([F:22])=[N:18][CH:19]=[CH:20][CH:21]=4)=[CH:9][CH:10]=3)[C@@:5]3([CH2:26][O:25][C:24]([NH2:27])=[N:23]3)[C:4]=2[CH:3]=1.[CH3:28][C:29]1[CH:33]=[C:32]([Sn](CCCC)(CCCC)CCCC)[O:31][N:30]=1.CC(N)CC1C=CC=CC=1.OP(O)(O)=O>>[F:22][C:17]1[C:16]([C:8]2[CH:9]=[CH:10][C:11]3[O:12][C:13]4[C:4](=[CH:3][C:2]([C:32]5[O:31][N:30]=[C:29]([CH3:28])[CH:33]=5)=[CH:15][CH:14]=4)[C@:5]4([CH2:26][O:25][C:24]([NH2:27])=[N:23]4)[C:6]=3[CH:7]=2)=[CH:21][CH:20]=[CH:19][N:18]=1

Komponenten

4

Edukt 3

HCID 62885Benzeneethanamine, alpha-methyl-, phosphate (1:1)HCID 27632553-Methyl-5-(tributylstannyl)isoxazoleHCID 67242922(S)-2'-bromo-7'-(2-fluoropyridin-3-yl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

Produkt 1

HCID 45254129(S)-2'-(2-fluoropyridin-3-yl)-7'-(3-methylisoxazol-5-yl)-5H-spiro[oxazole-4,9'-xanthen]-2-amine

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A resealable was charged with (S)-2′-bromo-7′-(2-fluoropyridin-3-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine (300 mg, 0.704 mmol), 3-methyl-5-(tributylstannyl)isoxazole (786 mg, 2.111 mmol), amphos (18.68 mg, 0.070 mmol) and argon purged dry dioxane (3 mL). The tube was purged with argon, sealed and heated with microwave at 100° C. for 1 h. The solution was concentrated. The crude product was purified via silica gel column chromatography (RediSep 12 g column) using 10-50% 90/10/1 DCM/MeOH/ammonia in DCM to afford (S)-2′-(2-fluoropyridin-3-yl)-7′-(3-methylisoxazol-5-yl)-5H-spiro[oxazole-4,9′-xanthen]-2-amine as a white solid. MS m/z=429.2 [M+H]+. Calcd for C24H17FN4O3: 428.42.

Aufarbeitung

  1. custompurged dry dioxane (3 mL)
  2. customThe tube was purged with argon
  3. customsealed
  4. concentrationThe solution was concentrated
  5. customThe crude product was purified via silica gel column chromatography (RediSep 12 g column)

Quellen und Nachweise

ORD-Eintrag
ord-aca068cc22304325ab971d337fbfb382
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08883782B2

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