3,5-Dimethoxybenzoic Acid → HCID 24956428、化合物

HRID 448056

反応式

HRID 448056 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[C:6]([OH:8])=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:6]([C:5]1[CH:9]=[C:10]([O:12][CH3:13])[CH:11]=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:8])[CH2:49][CH2:50][CH3:51]

参加物

5

反応物 4

HCID 143323,5-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 24956428HCID 24956428、化合物

実験手順

In a 20 mL vial 3,5-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 0.87-0.97 (m, 3 H) 1.28-1.37 (m, 2 H) 1.71-1.80 (m, 2 H) 2.46-2.48 (m, 3 H) 3.77-3.83 (m, 6 H) 4.23 (t, 2 H) 6.60-6.68 (m, 2 H) 7.10-7.14 (m, 2 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-069a05992a5f4d97b5128ec595a7c6b2
出典データセット
uspto-grants-2013_07
特許番号
US08481574B2

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