Diisopropylethylamine → Tert-butyl 3-(tert-butyldimethylsilyloxy)-5-((7-chloropyrido[4,3-b]pyrazin-5-ylamino)methyl)piperidine-1-carboxylate

HRID 57537Notes

Reaction equation

HRID 57537 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH:7]([O:9][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11])[CH2:6][N:5]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:4]1.Cl[C:25]1[C:34]2[C:29](=[N:30][CH:31]=[CH:32][N:33]=2)[CH:28]=[C:27]([Cl:35])[N:26]=1.CCN(C(C)C)C(C)C>C1COCC1>[Si:10]([O:9][CH:7]1[CH2:8][CH:3]([CH2:2][NH:1][C:25]2[C:34]3[C:29](=[N:30][CH:31]=[CH:32][N:33]=3)[CH:28]=[C:27]([Cl:35])[N:26]=2)[CH2:4][N:5]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:6]1)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 71113882Tert-butyl 3-(aminomethyl)-5-(tert-butyldimethylsilyloxy)piperidine-1-carboxylateHCID 717428275,7-Dichloropyrido(3,4-b)pyrazine

Product 1

HCID 86717367Tert-butyl 3-(tert-butyldimethylsilyloxy)-5-((7-chloropyrido[4,3-b]pyrazin-5-ylamino)methyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl 3-(aminomethyl)-5-(tert-butyldimethylsilyloxy)piperidine-1-carboxylate (4.74 g, 13.7 mmol), 5,7-dichloropyrido[4,3-b]pyrazine (2.75 g, 13.7 mmol) and DIPEA (2.12 g, 16.4 mmol) in THF (20 mL) was stirred at room temperature for 48 hours. The volatiles were removed under reduced pressure and the residue was treated with ethyl acetate, washed with brine, dried over Na2SO4, filtered, and concentrated to give the title compound.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. additionthe residue was treated with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ae9081071dd44d79a66c0acbafdd85e9
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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