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Hydrochloric Acid → (4S,6S)-4-(5-bromo-2-fluoropyridin-3-yl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine

HRID 930301
ノート
印刷プレビュー

反応式

HRID 930301 の反応式
C([N:9]([C:17]1[O:18][C@H:19]([C:32]([F:35])([F:34])[F:33])[CH2:20][C@:21]([C:24]2[C:25]([F:31])=[N:26][CH:27]=[C:28]([Br:30])[CH:29]=2)([CH3:23])[N:22]=1)C(=O)OC(C)(C)C)(=O)C1C=CC=CC=1.Cl>CO>[Br:30][C:28]1[CH:29]=[C:24]([C@:21]2([CH3:23])[CH2:20][C@@H:19]([C:32]([F:33])([F:34])[F:35])[O:18][C:17]([NH2:9])=[N:22]2)[C:25]([F:31])=[N:26][CH:27]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 86732129tert-Butyl benzoyl((4S,6S)-4-(5-bromo-2-fluoropyridin-3-yl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)carbamate

生成物 1

HCID 86732132(4S,6S)-4-(5-bromo-2-fluoropyridin-3-yl)-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine収率 65.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

The crude product (5k) from step 8 was dissolved in MeOH (5 mL). To this solution was added hydrogen chloride (4M in 1,4-dioxane; 8.0 mL, 32.0 mmol) and the reaction mixture was stirred at room temperature for 14 hours and was heated subsequently to 55° C. for 3.5 hours. The reaction mixture was concentrated, the residue was dissolved in water and the pH was adjusted to neutral with saturated sodium bicarbonate. The solution was extracted with DCM. The combined organic extracts were washed with brine and dried over sodium sulfate. The filtrate was concentrated and purified by silica gel column (gradient 0-5% MeOH/DCM) to afford the title compound (0.335 g, 0.941 mmol, 65.1% yield) as white solid. MS m/z=356, 358 [M]+/[M+2]+. Calculated for C11H10BrFF4N3O: 356.2

後処理

  1. temperaturewas heated subsequently to 55° C. for 3.5 hours
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in water
  4. extractionThe solution was extracted with DCM
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationThe filtrate was concentrated
  8. custompurified by silica gel column (gradient 0-5% MeOH/DCM)

出典と根拠

ORDレコード
ord-f11ff79a0db84a19a78668fe974f46a5
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09296734B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート