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Diisopropylethylamine → methyl 8-(1-(3,5-difluorophenylamino)ethyl)-2-((S)-3-methylmorpholino)-4-oxo-4H-chromene-6-carboxylate

HRID 1947375
ノート
印刷プレビュー

反応式

HRID 1947375 の反応式
[CH3:1][C@H:2]1[CH2:7][O:6][CH2:5][CH2:4][NH:3]1.[F:8][C:9]1[CH:10]=[C:11]([NH:16][CH:17]([C:19]2[CH:20]=[C:21]([C:34]([O:36][CH3:37])=[O:35])[CH:22]=[C:23]3[C:28]=2[O:27][C:26](S(CC)=O)=[CH:25][C:24]3=[O:33])[CH3:18])[CH:12]=[C:13]([F:15])[CH:14]=1.C(N(C(C)C)C(C)C)C>C(#N)C>[F:8][C:9]1[CH:10]=[C:11]([NH:16][CH:17]([C:19]2[CH:20]=[C:21]([C:34]([O:36][CH3:37])=[O:35])[CH:22]=[C:23]3[C:28]=2[O:27][C:26]([N:3]2[CH2:4][CH2:5][O:6][CH2:7][C@@H:2]2[CH3:1])=[CH:25][C:24]3=[O:33])[CH3:18])[CH:12]=[C:13]([F:15])[CH:14]=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

5

反応物 3

HCID 81531DiisopropylethylamineHCID 12012220(3S)-3-methylmorpholineHCID 58235048methyl 8-(1-(3,5-difluorophenylamino)ethyl)-2-(ethylsulfinyl)-4-oxo-4H-chromene-6-carboxylate

生成物 1

HCID 58235042methyl 8-(1-(3,5-difluorophenylamino)ethyl)-2-((S)-3-methylmorpholino)-4-oxo-4H-chromene-6-carboxylate収率 34.4%

試薬・触媒・溶媒 1

HCID 6342
Acetonitrile
溶媒

反応条件

温度
75 °C

実験手順

(S)-3-methylmorpholine (87 mg, 0.86 mmol) was added to a stirred solution of methyl 8-(1-(3,5-difluorophenylamino)ethyl)-2-(ethylsulfinyl)-4-oxo-4H-chromene-6-carboxylate (250 mg, 0.57 mmol) and N-ethyl-N-isopropylpropan-2-amine (0.150 mL, 0.86 mmol) in acetonitrile (3 mL) at RT. The resulting brown mixture was stirred at 75° C. for 7 hours. The reaction mixture was concentrated, diluted with DCM, washed with a 1M hydrochloric acid 1M, brine dried over magnesium sulfate and concentrated to afford the crude product which was purified by flash chromatography on silica gel eluting with 0 to 5% MeOH in DCM. The solvent was evaporated to dryness to afford methyl 8-(1-(3,5-difluorophenylamino)ethyl)-2-((S)-3-methylmorpholino)-4-oxo-4H-chromene-6-carboxylate (90 mg, 34%) as a yellow foam. Spectrum: [M−H]− 457.

後処理

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with DCM
  3. washwashed with a 1M hydrochloric acid 1M, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto afford the crude product which
  7. customwas purified by flash chromatography on silica gel eluting with 0 to 5% MeOH in DCM
  8. customThe solvent was evaporated to dryness

出典と根拠

ORDレコード
ord-49cecbeeb4204cba9cfa0da086d33973
出典データセット
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08399460B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート