Cyclopropylamine → HCID 90308860, compound

HRID 2283671Notes

Reaction equation

HRID 2283671 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([O-:10])=O)=[N:6][CH:7]=1.Cl[C:12]1[N:13]=[C:14]([S:23][CH3:24])[N:15]=[N:16][C:17]=1[C:18]([O:20][CH2:21][CH3:22])=[O:19].[CH:25]1([NH2:28])[CH2:27][CH2:26]1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CS(C)=O.C(OCC)(=O)C>[CH:25]1([NH:28][C:8]([C:5]2[N:6]=[CH:7][C:2]([NH:1][C:12]3[N:13]=[C:14]([S:23][CH3:24])[N:15]=[N:16][C:17]=3[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:3][CH:4]=2)=[O:10])[CH2:27][CH2:26]1

Participants

8

Reactant 5

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 7023052HCID 7023052, compoundHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11557703Ethyl 5-Chloro-3-(Methylthio)-1,2,4-Triazine-6-Carboxylate

Product 1

HCID 90308860HCID 90308860, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Aminopicolinate (44 mg) was added to a solution of ethyl 5-chloro-3-(methylthio)-1,2,4-triazine-6-carboxylate (70 mg) in dimethylsulfoxide (1.5 ml), and the reaction solution was stirred at room temperature for 10 minutes. Thereafter, cyclopropylamine (0.017 ml), diisopropylethylamine (0.079 ml), and HATU (125 mg) were successively added, and the reaction solution was stirred at room temperature overnight. The reaction solution was diluted with ethyl acetate, and washed successively with an aqueous sodium bicarbonate solution and a saturated saline solution. After drying over anhydrous sodium sulfate, the solvent was evaporated under vacuum. The resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate) to obtain ethyl 5-(6-(cyclopropylcarbamoyl)pyridin-3-ylamino)-3-(methylthio)-1,2,4-triazine-6-carboxylate.

Workup

  1. stirringthe reaction solution was stirred at room temperature overnight
  2. washwashed successively with an aqueous sodium bicarbonate solution
  3. dry with materialAfter drying over anhydrous sodium sulfate
  4. customthe solvent was evaporated under vacuum
  5. customThe resultant residue was purified by column chromatography on silica gel (developing solvent:hexane/ethyl acetate)

Sources & evidence

ORD record
ord-6e95b51751204f429e464b8ac5dc88a8
Source dataset
uspto-grants-2015_09
Patent number
US09145414B2

Reaction notes

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