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

HRID 448053

반응식

HRID 448053 반응식
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH3:11])[CH:10]=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-].[CH2:46]([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:5]([C:4]1[CH:8]=[C:9]([CH3:11])[CH:10]=[C:2]([CH3:1])[CH:3]=1)=[O:7])[CH2:47][CH2:48][CH3:49]

참가 물질

5

반응물 4

HCID 103563,5-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

생성물 1

HCID 24956425(2Z)-2-(3-butyl-5-methyl-1,3,4-thiadiazol-2(3H)-ylidene)-1-(3,5-dimethylphenyl)ethanone

실험 절차

In a 20 mL vial 3,5-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 0.87-0.96 (m, 3 H) 1.28-1.39 (m, 2 H) 1.68-1.80 (m, 2 H) 2.33 (s, 6 H) 2.47 (s, 3 H) 4.21 (t, 2 H) 6.66 (s, 1 H) 7.14 (s, 1 H) 7.62 (s, 2 H); MS (ESI) m/z 303 (M+H)+.

후처리

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

출처 및 근거

ORD 기록
ord-a3fcb23499344a848b78f35f246fb35d
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481574B2

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