Hydrochloric Acid → (S)-1-(1-(7-chloropyrido[4,3-b]pyrazin-5-yl)pyrrolidin-3-yl)ethanol
Reaction equation
[OH:1][CH:2]([C@H:4]1[CH2:8][CH2:7][N:6]([C:9](OC(C)(C)C)=O)[CH2:5]1)[CH3:3].Cl.CCN(C(C)C)C(C)C.ClC1[C:36]2[C:31](=[N:32][CH:33]=[CH:34][N:35]=2)[CH:30]=[C:29]([Cl:37])[N:28]=1>C1COCC1>[Cl:37][C:29]1[N:28]=[C:9]([N:6]2[CH2:7][CH2:8][CH:4]([C@@H:2]([OH:1])[CH3:3])[CH2:5]2)[C:36]2[C:31](=[N:32][CH:33]=[CH:34][N:35]=2)[CH:30]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
(S)-tert-butyl 3-(1-hydroxyethyl)pyrrolidine-1-carboxylate was treated with HCl solution (in EtOAc, 5 mL) at room temperature for 2 hours. The volatiles were removed under reduced pressure, and the residue was dissolved in anhydrous THF (10 mL). To the resulted THF solution, DIPEA (570 mg, 4.4 mmol) and 5,7-dichloropyrido[4,3-b]pyrazine (400 mg, 2.0 mmol) were added, and the reaction was stirred at room temperature overnight. The volatiles were removed under reduced pressure, and the residue was dissolved in ethyl acetate, washed with brine and dried over Na2SO4, filtered, and concentrated. The residue was purified by chromatography to afford the title compound. MS (m/z): 279 (M+H)+.
Workup
- customThe volatiles were removed under reduced pressure
- dissolutionthe residue was dissolved in anhydrous THF (10 mL)
- customThe volatiles were removed under reduced pressure
- dissolutionthe residue was dissolved in ethyl acetate
- washwashed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customThe residue was purified by chromatography
Sources & evidence
- ORD record
- ord-505c00e440b949ee81e2a8ae92c5d312
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434726B2
Reaction notes
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