2,3-Dimethoxybenzoic acid → (2Z)-2-(3-butyl-5-methyl-1,3,4-thiadiazol-2(3H)-ylidene)-1-(2,3-dimethoxyphenyl)ethanone

HRID 448054ノート

反応式

HRID 448054 の反応式
[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:4]=1[C:5]([OH:7])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[I-].[CH2:48]([N+:52]1[N:56]=[C:55]([CH3:57])[S:54][C:53]=1[CH3:58])[CH2:49][CH2:50][CH3:51]>>[CH2:48]([N:52]1[N:56]=[C:55]([CH3:57])[S:54]/[C:53]/1=[CH:58]\[C:5]([C:4]1[CH:8]=[CH:9][CH:10]=[C:11]([O:12][CH3:13])[C:3]=1[O:2][CH3:1])=[O:7])[CH2:49][CH2:50][CH3:51]

参加物

5

反応物 4

HCID 152042,3-Dimethoxybenzoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 691879173-Butyl-2,5-dimethyl-1,3,4-thiadiazol-3-ium iodide

生成物 1

HCID 24956426(2Z)-2-(3-butyl-5-methyl-1,3,4-thiadiazol-2(3H)-ylidene)-1-(2,3-dimethoxyphenyl)ethanone

実験手順

In a 20 mL vial 2,3-dimethoxybenzoic acid (0.9 mL of 0.2 M in DMA, 1.10 equiv) was added followed by the addition of HATU (76 mg in 0.7 mL of DMA, 0.2 mmol, 1.20 equiv.), DIEA (51 mg in 0.7 mL of DMA, 0.4 mmol, 2.40 equiv.), and finally 3-butyl-2,5-dimethyl-1,3,4-thiadiazol-3-ium iodide (49 mg in 0.7 mL of DMA, 0.17 mmol, 1 equiv.). The mixture was shaken overnight at room temperature and then concentrated in vacuo. The resulting residue was taken up in 1:1 DMSO/MeOH and purified by reverse phase HPLC using a method analogous to that described in Example 53 to provide the title compound. 1H NMR (500 MHz, DMSO-d6/D2O) δ ppm 0.86-0.95 (m, 3 H) 1.27-1.38 (m, 2 H) 1.71-1.77 (m, 2 H) 2.48 (s, 3 H) 3.75 (s, 3 H) 3.80 (s, 3 H) 4.10-4.14 (m, 2 H) 6.45 (s, 1 H) 7.08-7.19 (m, 3 H); MS (ESI) m/z 335 (M+H)+.

後処理

  1. concentrationconcentrated in vacuo
  2. custompurified by reverse phase HPLC

出典と根拠

ORDレコード
ord-3e483ed418954f72965d88ea29828d9e
出典データセット
uspto-grants-2013_07
特許番号
US08481574B2

反応ノート

読み込み中…