Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → HCID 131730522, compound

HRID 1969891Notes

Reaction equation

HRID 1969891 reaction equation
[NH:1]([C:3]1[N:4]=[C:5]2[CH:11]=[CH:10][N:9]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:6]2=[N:7][CH:8]=1)[NH2:2].[C:22]([O:26][C:27]([N:29]1[CH2:33][C@H:32]([CH2:34][CH3:35])[C@H:31]([C:36](O)=[O:37])[CH2:30]1)=[O:28])([CH3:25])([CH3:24])[CH3:23].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl>[CH2:34]([C@H:32]1[C@@H:31]([C:36]([NH:2][NH:1][C:3]2[N:4]=[C:5]3[CH:11]=[CH:10][N:9]([S:12]([C:15]4[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=4)(=[O:13])=[O:14])[C:6]3=[N:7][CH:8]=2)=[O:37])[CH2:30][N:29]([C:27]([O:26][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:28])[CH2:33]1)[CH3:35]

Participants

5

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 580098102-Hydrazinyl-5-tosyl-5H-pyrrolo[2,3-b]pyrazineHCID 67999007HCID 67999007, compound

Product 1

HCID 131730522HCID 131730522, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a suspension of 2-hydrazinyl-5-tosyl-5H-pyrrolo[2,3-b]pyrazine (5.00 g, 16.48 mmol, Example 1, Step D) and (cis)-1-(tert-butoxycarbonyl)-4-ethylpyrrolidine-3-carboxylic acid (4.01 g, 16.48 mmol) in DCM (70 mL) were added TEA (5.75 mL, 41.2 mmol) and HATU (6.90 g, 18.15 mmol, Novabiochem). The resulting suspension was stirred at about 25° C. for about 2 h. The reaction mixture was transferred to a separatory funnel and washed with saturated aqueous NaHCO3 (4×30 mL). The organic layer was dried over anhydrous MgSO4, filtered, and concd in vacuo to give a brown foam. The crude material was purified via flash chromatography on silica gel by dry loading the compound onto the column and eluting with 50-100% EtOAc in DCM/petroleum ether (1:1) to afford (cis)-tert-butyl 3-ethyl-4-(2-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)hydrazinecarbonyl)pyrrolidine-1-carboxylate with EtOAc as an excipient (9.41 g, 100%) as a tan foam: LC/MS (Table 1, Method a) Rt=2.45 min; MS m/z: 529 (M+H)+.

Workup

  1. customThe reaction mixture was transferred to a separatory funnel
  2. washwashed with saturated aqueous NaHCO3 (4×30 mL)
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. customconcd in vacuo to give a brown foam
  6. customThe crude material was purified via flash chromatography on silica gel
  7. customby dry loading the compound onto the column
  8. washeluting with 50-100% EtOAc in DCM/petroleum ether (1:1)

Sources & evidence

ORD record
ord-72962bce04164b7d9236d3168503113b
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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