Diethyl Pyrocarbonate → HCID 78320527, 화합물

HRID 1479827노트

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HRID 1479827 반응식
[Cl:1][C:2]1[S:6][C:5]([S:7]([N:10]([CH2:34][CH3:35])[C:11](=[CH2:33])[C:12](NCC2C=CN=C(C3C=CC(OC(F)(F)F)=CC=3)C=2)=[O:13])(=[O:9])=[O:8])=[CH:4][CH:3]=1.CCOC(OC(OCC)=O)=O.[N:47]1([C:52]2[CH:57]=[C:56]([CH2:58][NH2:59])[CH:55]=[C:54]([C:60]3[CH:65]=[CH:64][C:63]([C:66]([F:69])([F:68])[F:67])=[CH:62][CH:61]=3)[N:53]=2)[CH2:51][CH2:50][CH2:49][CH2:48]1>C1COCC1>[Cl:1][C:2]1[S:6][C:5]([S:7]([N:10]([CH2:34][CH3:35])[C:11](=[CH2:33])[C:12]([NH:59][CH2:58][C:56]2[CH:55]=[C:54]([C:60]3[CH:65]=[CH:64][C:63]([C:66]([F:69])([F:67])[F:68])=[CH:62][CH:61]=3)[N:53]=[C:52]([N:47]3[CH2:51][CH2:50][CH2:49][CH2:48]3)[CH:57]=2)=[O:13])(=[O:9])=[O:8])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 3051Diethyl PyrocarbonateHCID 66832317HCID 66832317, 화합물HCID 783199132-[(5-chloro-2-thienyl)sulfonyl-ethyl-amino]N-[[2-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methyl]prop-2-enamide

생성물 1

HCID 78320527HCID 78320527, 화합물수율 25%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Acid 7 (295.76 mg, 1 mmol) was dissolved in 10 ml of THF and at rt DEPC (1.1 equiv, 0.15 ml) and [2-pyrrolidin-1-yl-6-[4-(trifluoromethyl)phenyl]-4-pyridyl]methanamine 27A (1.1 equiv., 353.47 mg) were added to the solution. The mixture was stirred at rt overnight then evaporated. The residue was dissolved in AcOEt (30 ml) and washed with water (1×20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude by chromatographic column (3:7 EtOAc:petroleum ether) afforded 150 mg of a pale yellow solid. Yield=25% 1HNMR (DMSO, 200 MHz) δ 1.07 (3H, t), 1.94 (4H, m), 3.41 (6H, m), 4.37 (2H, d), 5.39 (1H, s), 6.21 (1H, s), 6.31 (1H, s), 7.20 (1H, s), 7.34 (1H, d, J=4.2 Hz), 7.57 (1H, d, J=4 Hz), 7.91 (2H, d), 8.48 (2H, d), 8.75 (1H, bt) [M+1] 599.9 (C26H26ClF3N4O3S2 requires 599.09).

후처리

  1. additionwere added to the solution
  2. customthen evaporated
  3. dissolutionThe residue was dissolved in AcOEt (30 ml)
  4. washwashed with water (1×20 ml) and brine
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe purification of the crude by chromatographic column (3:7 EtOAc:petroleum ether)

출처 및 근거

ORD 기록
ord-4359018152d64239bc1dea9b4fbafb15
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409864B2

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