Diisopropylethylamine → HCID 24956782, compound

HRID 448063Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[CH3:12])[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-].[CH2:47]([N+:51]1[N:55]=[C:54]([CH3:56])[S:53][C:52]=1[CH3:57])[CH2:48][CH2:49][CH3:50]>>[CH2:47]([N:51]1[N:55]=[C:54]([CH3:56])[S:53]/[C:52]/1=[CH:57]\[C:6]([C:5]1[CH:9]=[CH:10][C:11]([CH3:12])=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:8])[CH2:48][CH2:49][CH3:50]

Participants

Reactant 4

HCID 81531Diisopropylethylamine

HCID 815794-Methyl-m-anisic acid

HCID 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 24956782HCID 24956782, compound

Procedure

In a 20 mL vial 3-methoxy-4-methylbenzoic 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 0.89-0.94 (m, 3 H) 1.29-1.37 (m, 2 H) 1.71-1.79 (m, 2 H) 2.20 (s, 3 H) 2.48 (s, 3H) 3.85 (s, 3 H) 4.23 (t, 2 H) 6.67 (s, 1 H) 7.22 (d, 1 H) 7.48 (s, 1 H) 7.53 (d, 1 H); MS (ESI) m/z 319 (M+H)+.

Workup

concentrationconcentrated in vacuo
custompurified by reverse phase HPLC

Sources & evidence

ORD record: ord-9e7dbf77aafd478985c4b7f6568d4ccb
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481574B2

Reaction notes

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