Propionic Acid → HCID 66580430, 화합물

HRID 1521873노트

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HRID 1521873 반응식
[OH:1][N:2]=[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N:11]2[C:15]3[C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=4[S:22](=[O:25])(=[O:24])[CH2:23][C:14]=3[C:13]([C:26]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[O:27])=[N:12]2)[CH:6]=1)[NH2:4].[C:34](O)(=O)[CH2:35][CH3:36]>CCOC(C)=O>[CH2:35]([C:36]1[O:1][N:2]=[C:3]([C:5]2[CH:6]=[C:7]([N:11]3[C:15]4[C:16]5[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=5[S:22](=[O:24])(=[O:25])[CH2:23][C:14]=4[C:13]([C:26]([N:28]4[CH2:33][CH2:32][O:31][CH2:30][CH2:29]4)=[O:27])=[N:12]3)[CH:8]=[CH:9][CH:10]=2)[N:4]=1)[CH3:34]

참가 물질

4

반응물 2

HCID 1032Propionic AcidHCID 86670899HCID 86670899, 화합물

생성물 1

HCID 66580430HCID 66580430, 화합물

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

To a solution of N′-hydroxy-3-[3-(morpholin-4-ylcarbonyl)-5,5-dioxidothiochromeno[4,3-c]pyrazol-1(4H)-yl]benzenecarboximidamide (150 mg, 0.32 mmol) in dry EtOAc is added propionic acid (13 μl, 0.32 mmol) under nitrogen followed by TEA (0.13 mL, 0.963 mmol) and propane phosphonic acid cyclic anhydride (0.51 mL, 0.80 mmol) at 0° C. under nitrogen. The reaction mixture is heated to 80° C. for 12 h under nitrogen and concentrated under vacuum. Solid residue is purified by silica gel column chromatography (1.2% MeOH in DCM) to afford the title compound as an off white solid. 1H NMR (DMSO-d6, 400 MHz): δ 8.24-8.22 (d, J=7.4 Hz, 1H), 8.05-8.02 (m, 2H), 7.81-7.77 (m, 2H), 7.64 (m, 1H), 7.57 (m, 1H), 6.93-6.91 (d, J=7.9 Hz, 1H), 4.91 (s, 2H), 3.92-3.90 (m, 2H), 3.67 (m, 4H), 3.61-3.60 (m, 2H), 3.02-3.0 (m, 2H), 1.33-1.29 (t, J=7.6 Hz, 3H). MS (ESI+): 506.0. HPLC (max plot) 97.13%; Rt 4.34 min.

후처리

  1. concentrationconcentrated under vacuum
  2. customSolid residue is purified by silica gel column chromatography (1.2% MeOH in DCM)

출처 및 근거

ORD 기록
ord-235733a77e0749a09e1dbc5a04b12a3e
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09073940B2

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