Tetrabutylammonium Fluoride → 3-N,N-bis(4-methoxybenzyl)-1-trityl-1H-pyrazolo[4,3-c]pyridine-3,6-diamine

HRID 590884Notes

Reaction equation

HRID 590884 reaction equation
[CH3:1][O:2][C:3]1[CH:51]=[CH:50][C:6]([CH2:7][N:8]([CH2:41][C:42]2[CH:47]=[CH:46][C:45]([O:48][CH3:49])=[CH:44][CH:43]=2)[C:9]2[C:13]3[CH:14]=[N:15][C:16]([NH:18]C(=O)[O-])=[CH:17][C:12]=3[N:11]([C:22]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:10]=2)=[CH:5][CH:4]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]([CH2:41][C:42]2[CH:43]=[CH:44][C:45]([O:48][CH3:49])=[CH:46][CH:47]=2)[C:9]2[C:13]3[CH:14]=[N:15][C:16]([NH2:18])=[CH:17][C:12]=3[N:11]([C:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:10]=2)=[CH:50][CH:51]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131734503(3-(bis(4-methoxybenzyl)amino)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate

Product 1

HCID 1182723773-N,N-bis(4-methoxybenzyl)-1-trityl-1H-pyrazolo[4,3-c]pyridine-3,6-diamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3-(bis(4-methoxybenzyl)amino)-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-yl)carbamate (0.4 g, 0.55 mmol) in THF (8 mL) was added TBAF (1.0 M solution in THF, 10 mL) and the contents were heated to reflux. After 12 h, the reaction was cooled back to ambient temperature, quenched with 1N HCl (5 mL) and stirred at ambient temperature for 1 h. The reaction mixture was further diluted with EtOAc (25 mL) and the organic layer was separated. The organic layer was washed with brine (1×20 mL), dried over anhydrous Na2SO4 and the solvents were removed under reduced pressure. The residue thus obtained was purified by a filter column to afford the title compound. MS ES calc'd. for C41F137N5O2 [M+H]+ 632. Found 632.

Workup

  1. temperaturethe contents were heated to reflux
  2. customquenched with 1N HCl (5 mL)
  3. additionThe reaction mixture was further diluted with EtOAc (25 mL)
  4. customthe organic layer was separated
  5. washThe organic layer was washed with brine (1×20 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. customthe solvents were removed under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by a filter column

Sources & evidence

ORD record
ord-6412d951d9bf447f84bd9a4caad1e381
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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