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

反応式

HRID 335784 の反応式
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

参加物

4

反応物 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

生成物 1

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

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-aca068cc22304325ab971d337fbfb382
出典データセット
uspto-grants-2014_11
特許番号
US08883782B2

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