Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 86722696, compound

HRID 1480478Notes

Reaction equation

HRID 1480478 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([CH2:13][CH2:14][NH2:15])[N:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:16][C:17]1[CH:18]=[C:19]([CH:34]=[C:35]([Cl:37])[CH:36]=1)[CH2:20][O:21][C:22]([N:24]1[CH2:29][CH2:28][CH:27]([CH2:30][C:31](O)=[O:32])[CH2:26][CH2:25]1)=[O:23].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][CH2:14][NH:15][C:31](=[O:32])[CH2:30][CH:27]2[CH2:28][CH2:29][N:24]([C:22]([O:21][CH2:20][C:19]3[CH:18]=[C:17]([Cl:16])[CH:36]=[C:35]([Cl:37])[CH:34]=3)=[O:23])[CH2:25][CH2:26]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 836380801-(Phenylmethyl)-1H-1,2,3-triazole-4-ethanamineHCID 86722695HCID 86722695, compound

Product 1

HCID 86722696HCID 86722696, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A reaction mixture comprising of 2-(1-benzyl-1H-1,2,3-triazol-4-yl)ethanamine (59.1 mg, 0.292 mmol), 2-(1-(((3,5-dichlorobenzyl)oxy)carbonyl)piperidin-4-yl)acetic acid (101 mg, 0.292 mmol), HATU (222 mg, 0.584 mmol) and TEA (122 μl, 0.877 mmol) in DMF (0.97 ml) was stirred for 3 hours at room temperature. The reaction mixture was diluted with water and ethyl acetate. The organic layer was removed 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 removed
  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-89c4d12a78544dd9a37523e48737e342
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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