tert-butyl 4-(4-amino-6-(3-(pyrrolidin-1-yl)propyl)pyrrolo[2,1-f][1,2,4]triazin-7-yl)-5,6-dihydropyridine-1(2H)-carboxylate → Tert-butyl 4-(4-amino-6-(3-(pyrrolidin-1-yl)propyl)pyrrolo[2,1-f][1,2,4]triazin-7-yl)piperidine-1-carboxylate

HRID 1615468Notes

Reaction equation

HRID 1615468 reaction equation
[NH2:1][C:2]1[C:7]2=[CH:8][C:9]([CH2:24][CH2:25][CH2:26][N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)=[C:10]([C:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH:12]=3)[N:6]2[N:5]=[CH:4][N:3]=1>C([O-])(=O)C.[Pt](=O)=O>[NH2:1][C:2]1[C:7]2=[CH:8][C:9]([CH2:24][CH2:25][CH2:26][N:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)=[C:10]([CH:11]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 66601711tert-butyl 4-(4-amino-6-(3-(pyrrolidin-1-yl)propyl)pyrrolo[2,1-f][1,2,4]triazin-7-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 66614420Tert-butyl 4-(4-amino-6-(3-(pyrrolidin-1-yl)propyl)pyrrolo[2,1-f][1,2,4]triazin-7-yl)piperidine-1-carboxylateYield 100.1%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 175AcetateSolvent

Procedure

In a pressure reactor (50 mL), a mixture of the compound (132 mg, 0.31 mmol) prepared in Example 17 and platinum (IV) oxide in acetyl hydroxide (10 mL) was stirred under hydrogen atmosphere (3 atm). At 6 hours, the mixture was filtered through celite, eluting with acetyl hydroxide. The solvent was removed in vacuo. The resulting material extracted with DCM/sodium bicarbonate aqueous solution. The organic layers were dried over sodium sulfate, filtered and the solvent removed in vacuum to obtain the title compound (133 mg) having the following physical data.

Workup

  1. filtrationthe mixture was filtered through celite
  2. washeluting with acetyl hydroxide
  3. customThe solvent was removed in vacuo
  4. extractionThe resulting material extracted with DCM/sodium bicarbonate aqueous solution
  5. dry with materialThe organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. customthe solvent removed in vacuum

Sources & evidence

ORD record
ord-0e9a2bccad184a8e878e419f8f6f8ad1
Source dataset
uspto-grants-2014_07
Patent number
US08765754B2

Reaction notes

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