Hydrochloric Acid → N-((5,5-difluoropiperidin-3-yl)methyl)-7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-amine

HRID 57615

Reaction equation

HRID 57615 reaction equation
[F:1][C:2]1([F:39])[CH2:7][CH:6]([CH2:8][NH:9][C:10]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][N:18]=3)[CH:13]=[C:12]([C:20]3[CH:25]=[CH:24][C:23]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)=[CH:22][CH:21]=3)[N:11]=2)[CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.Cl>>[F:39][C:2]1([F:1])[CH2:3][NH:4][CH2:5][CH:6]([CH2:8][NH:9][C:10]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][N:18]=3)[CH:13]=[C:12]([C:20]3[CH:21]=[CH:22][C:23]([N:26]4[CH2:27][CH2:28][O:29][CH2:30][CH2:31]4)=[CH:24][CH:25]=3)[N:11]=2)[CH2:7]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 71113804Tert-butyl 3,3-difluoro-5-((7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)piperidine-1-carboxylate

Product 1

HCID 71113816N-((5,5-difluoropiperidin-3-yl)methyl)-7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-amine

Procedure

tert-Butyl 3,3-difluoro-5-((7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)piperidine-1-carboxylate from step A (227 mg, 0.42 mmol) was treated with HCl solution (in EtOAc, 5 N) at room temperature until the reaction was finished. The volatiles were removed under reduced pressure, dissolved in dichloromethane (5 mL), and neutralized with ammonium hydroxide. The dichloromethane phase was concentrated to afford N-((5,5-difluoropiperidin-3-yl)methyl)-7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-amine. MS (m/z): 441 (M+H)+.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. dissolutiondissolved in dichloromethane (5 mL)
  3. concentrationThe dichloromethane phase was concentrated

Sources & evidence

ORD record
ord-75b30ea9a5ba40a6bc265c2846b58848
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Linked notes

Loading…