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

HRID 572814
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HRID 572814 반응식
[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
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5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

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온도
75 °C

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-6aae7f0fa1e14e96a62d83d88b845e9b
출처 데이터셋
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09029374B2

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