Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 86722694, compound

HRID 1480474Notes

Reaction equation

HRID 1480474 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([CH2:13][NH2:14])[N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:34]=[C:35]([Cl:37])[CH:36]=1)[CH2:19][O:20][C:21]([N:23]1[CH2:28][CH2:27][CH:26]([CH2:29][CH2:30][C:31](O)=[O:32])[CH2:25][CH2:24]1)=[O:22].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O.C(OCC)(=O)C>[CH2:1]([N:8]1[CH:12]=[C:11]([CH2:13][NH:14][C:31](=[O:32])[CH2:30][CH2:29][CH:26]2[CH2:25][CH2:24][N:23]([C:21]([O:20][CH2:19][C:18]3[CH:34]=[C:35]([Cl:37])[CH:36]=[C:16]([Cl:15])[CH:17]=3)=[O:22])[CH2:28][CH2:27]2)[N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 12160907HCID 12160907, compoundHCID 86722693HCID 86722693, compound

Product 1

HCID 86722694HCID 86722694, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A reaction mixture comprising of (1-benzyl-1H-1,2,3-triazol-4-yl)methanamine (46.2 mg, 0.245 mmol), 3-(1-(((3,5-dichlorobenzyl)oxy)carbonyl)piperidin-4-yl)propanoic acid (88 mg, 0.245 mmol), HATU (187 mg, 0.491 mmol) and TEA (103 μl, 0.736 mmol) in DMF (0.8 ml) was stirred for 2 hours at room temperature. The reaction mixture was diluted with water and ethyl acetate. The organic layer was separated and dried over MgSO4, filtered and concentrated under reduced pressure. Further purification was carried out using preparative LC-MS. The resulting product fractions were concentrated under reduced pressure to give aqueous solutions which were extracted with ethyl acetate. The organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure to afford the title compound.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customFurther purification
  6. concentrationThe resulting product fractions were concentrated under reduced pressure
  7. customto give aqueous solutions which
  8. extractionwere extracted with ethyl acetate
  9. dry with materialThe organic extracts were dried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3dc909e56fba4e0a9bf3f6ca649162af
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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