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

HRID 448051

反応式

HRID 448051 の反応式
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([OH:6])=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-].[CH2:46]([N+:50]1[N:54]=[C:53]([CH3:55])[S:52][C:51]=1[CH3:56])[CH2:47][CH2:48][CH3:49]>>[CH2:46]([N:50]1[N:54]=[C:53]([CH3:55])[S:52]/[C:51]/1=[CH:56]\[C:4]([C:3]1[CH:7]=[C:8]([CH3:11])[CH:9]=[CH:10][C:2]=1[CH3:1])=[O:6])[CH2:47][CH2:48][CH3:49]

参加物

5

反応物 4

HCID 118922,5-Dimethylbenzoic 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 24956423(2Z)-2-(3-butyl-5-methyl-1,3,4-thiadiazol-2(3H)-ylidene)-1-(2,5-dimethylphenyl)ethanone

実験手順

In a 20 mL vial 2,5-dimethylbenzoic 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 0.84-0.94 (m, 3 H) 1.27-1.33 (m, 2 H) 1.68-1.77 (m, 2 H) 2.30 (s, 6 H) 2.48 (s, 3 H) 4.12 (t, 2 H) 6.20 (1, 1 H) 7.10 (s, 2 H) 7.28 (s, 1 H); MS (ESI) m/z 303 (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-e70ef20b76dc4d00ba6347f738c75ece
出典データセット
uspto-grants-2013_07
特許番号
US08481574B2

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