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

HRID 57601Notes

Reaction equation

HRID 57601 reaction equation
[NH2:1][CH2:2][C@@H:3]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.Cl[C:17]1[C:26]2[C:21](=[N:22][CH:23]=[CH:24][N:25]=2)[CH:20]=[C:19]([Cl:27])[N:18]=1.CCN(C(C)C)C(C)C>C1COCC1>[Cl:27][C:19]1[N:18]=[C:17]([NH:1][CH2:2][C@@H:3]2[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]2)[C:26]2[C:21](=[N:22][CH:23]=[CH:24][N:25]=2)[CH:20]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1502022tert-Butyl (3S)-3-(aminomethyl)piperidine-1-carboxylateHCID 717428275,7-Dichloropyrido(3,4-b)pyrazine

Product 1

HCID 86717378(S)-tert-butyl 3-((7-chloropyrido[4,3-b]pyrazin-5-ylamino)methyl)piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (S)-tert-butyl 3-(aminomethyl)piperidine-1-carboxylate (100 mg, 0.5 mmol), 5,7-dichloropyrido[4,3-b]pyrazine (100 mg, 0.5 mmol) and DIPEA (77 mg, 0.6 mmol) in THF (5 mL) was stirred at room temperature for 4 hours. The volatiles were removed under reduced pressure, and the residue was treated with ethyl acetate, with brine, and concentrated to give the crude title compound.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. additionthe residue was treated with ethyl acetate, with brine
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-b1bcd696f65f4308afcb0721a18dd815
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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