Triethylamine → HCID 178426491, compound

HRID 707432Notes

Reaction equation

HRID 707432 reaction equation
[Cl:1][C:2]1[C:3]([C:8]([CH3:13])([CH3:12])[C:9]([OH:11])=O)=[N:4][CH:5]=[CH:6][N:7]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[CH3:45][C:46]1[CH:47]=[CH:48][C:49]([NH:52][C@H:53]2[CH2:58][CH2:57][C@@H:56]([NH2:59])[CH2:55][CH2:54]2)=[N:50][CH:51]=1>C(Cl)Cl>[Cl:1][C:2]1[C:3]([C:8]([CH3:13])([CH3:12])[C:9]([NH:59][C@H:56]2[CH2:55][CH2:54][C@@H:53]([NH:52][C:49]3[CH:48]=[CH:47][C:46]([CH3:45])=[CH:51][N:50]=3)[CH2:58][CH2:57]2)=[O:11])=[N:4][CH:5]=[CH:6][N:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866941182-(3-Chloropyrazin-2-yl)-2-methylpropanoic acidHCID 178426488HCID 178426488, compound

Product 1

HCID 178426491HCID 178426491, compoundYield 20.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round bottomed flask was added 2-(3-chloropyrazin-2-yl)-2-methylpropanoic acid (0.267 g, 1.333 mmol, 00388), 2-(3H-[1,2,3]triazolo[4,5-b]pyridin-3-yl)-1,1,3,3-tetramethylisouronium hexafluorophosphate(V) (0.659 g, 1.733 mmol, GenScript) and triethylamine (0.743 ml, 5.33 mmol, Sigma-Aldrich Chemical Company, Inc.) in DCM (4.44 ml). cis-N1-(5-Methylpyridin-2-yl)cyclohexane-1,4-diamine (0.3709 g, 1.333 mmol) was added and the reaction was allowed to stir at room temperature for 4 h. Solvent was evaporated in vacuo. The crude product was adsorbed onto a plug of silica gel and chromatographed through a Biotage SNAP HP-silica gel column (50 g), eluting with a gradient of 10% to 100% EtOAc in hexane to give the title compound (105.0 mg, 0.271 mmol, 20.3% yield). Product peak was found at 1.438 min (m+1=388.0). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.45-1.67 (m, 12 H) 1.75 (d, J=4.89 Hz, 2 H) 2.08 (s, 3 H) 3.68 (br. s., 1 H) 3.76 (br. s., 1 H) 6.50 (d, J=8.41 Hz, 1 H) 7.14-7.28 (m, 2 H) 7.76 (s, 1 H) 8.42 (d, J=2.54 Hz, 1 H) 8.65 (d, J=2.54 Hz, 1 H)

Workup

  1. customSolvent was evaporated in vacuo
  2. customchromatographed through a Biotage SNAP HP-silica gel column (50 g)
  3. washeluting with a gradient of 10% to 100% EtOAc in hexane

Sources & evidence

ORD record
ord-7f795e5846fe4ea19df279e08e2ab6f7
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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