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Hydrochloric Acid → 4-[4-(4,5-Dihydro-5-phenyl-3-isoxazolyl)-2-thiazolyl]-1,2,3,6-tetrahydro-1-(phenylmethyl)pyridine

HRID 1528555
ノート
印刷プレビュー

反応式

HRID 1528555 の反応式
[C:1]1([CH:7]2[O:11][N:10]=[C:9]([C:12]3[N:13]=[C:14]([C:17]4[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=4)[S:15][CH:16]=3)[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[BH4-].[Na+].Cl>C1(C)C=CC=CC=1.O>[C:1]1([CH:7]2[O:11][N:10]=[C:9]([C:12]3[N:13]=[C:14]([C:17]4[CH2:18][CH2:19][N:20]([CH2:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)[CH2:21][CH:22]=4)[S:15][CH:16]=3)[CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 4311764Sodium borohydrideHCID 687460464-[4-(4,5-Dihydro-5-phenyl-3-isoxazolyl)-2-thiazolyl]pyridine2 回

生成物 1

HCID 687439224-[4-(4,5-Dihydro-5-phenyl-3-isoxazolyl)-2-thiazolyl]-1,2,3,6-tetrahydro-1-(phenylmethyl)pyridine

試薬・触媒・溶媒 2

HCID 962
Water
溶媒
HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

To a solution of 4-[4-(4,5-dihydro-5-phenyl-3-isoxazolyl)-2-thiazolyl]pyridine (i.e. the product of Example 13, Step A) (0.60 g, 1.95 mmol) in toluene (10 mL) was added benzyl bromide (0.670 g, 3.90 mmol), and the reaction mixture was heated to 100° C. for 12 h. Then the reaction mixture was cooled to room temperature. The solid that precipitated out was filtered and dried. The solid was dissolved in methanol (10 mL), and sodium borohydride (0.072 g, 1.95 mmol) was added in portions. The reaction mixture was stirred at room temperature for 2 h, diluted with water (50 mL), neutralized with 1.5 N aqueous hydrochloric acid solution, and extracted with ethyl acetate (50 mL). The organic layer was separated, washed with brine (25 mL), and concentrated under reduced pressure. The residue was purified by medium-pressure liquid chromatography using 3% of methanol in chloroform as eluant to give 0.4 g of the title compound as a white solid.

後処理

  1. temperatureThen the reaction mixture was cooled to room temperature
  2. customThe solid that precipitated out
  3. filtrationwas filtered
  4. customdried
  5. dissolutionThe solid was dissolved in methanol (10 mL)
  6. extractionextracted with ethyl acetate (50 mL)
  7. customThe organic layer was separated
  8. washwashed with brine (25 mL)
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by medium-pressure liquid chromatography

出典と根拠

ORDレコード
ord-8ea16faf1c37487380246de7ab5cd9b9
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09090604B2

反応ノート

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