Diisopropylethylamine → (2Z)-2-(3-butyl-5-methyl-1,3,4-thiadiazol-2(3H)-ylidene)-1-(3-methylthien-2-yl)ethanone

HRID 448040Notes

Reaction equation

HRID 448040 reaction equation
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([OH:9])=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-].[CH2:44]([N+:48]1[N:52]=[C:51]([CH3:53])[S:50][C:49]=1[CH3:54])[CH2:45][CH2:46][CH3:47]>>[CH2:44]([N:48]1[N:52]=[C:51]([CH3:53])[S:50]/[C:49]/1=[CH:54]\[C:7]([C:3]1[S:4][CH:5]=[CH:6][C:2]=1[CH3:1])=[O:9])[CH2:45][CH2:46][CH3:47]

Participants

5

Reactant 4

HCID 81531DiisopropylethylamineHCID 902693-Methyl-2-thenoic acidHCID 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

Product 1

HCID 24955700(2Z)-2-(3-butyl-5-methyl-1,3,4-thiadiazol-2(3H)-ylidene)-1-(3-methylthien-2-yl)ethanone

Procedure

In a 20 mL vial 3-methylthiophene-2-carboxylic acid (0.9 mL of 0.2 M in DMA, 1.10 equiv) was added followed by the addition of HATU (77 mg in 0.7 mL of DMA, 0.2 mmol, 1.20 equiv.), DIEA (53 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 (50 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 0.92 (t, 3H) 1.28-1.39 (m, 2 H) 1.69-1.79 (m, 2 H) 2.45-2.48 (m, 3 H) 4.15 (t, 2 H) 6.18-6.22 (m, 1 H) 6.97 (d, 1 H) 7.55 (d, 1 H); MS (ESI) m/z 295 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-06d2e5d1e063416ca426a7fc7ce512ac
Source dataset
uspto-grants-2013_07
Patent number
US08481574B2

Reaction notes

Loading…