Diethyl Pyrocarbonate → HCID 78320527、化合物

HRID 1479827ノート

反応式

HRID 1479827 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 78320527HCID 78320527、化合物収率 25%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-4359018152d64239bc1dea9b4fbafb15
出典データセット
uspto-grants-2016_08
特許番号
US09409864B2

反応ノート

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