Hydrochloric Acid → (S)-1-(4-(5-(morpholin-2-ylmethylamino)pyrido[4,3-b]pyrazin-7-yl)phenyl)piperidin-4-ol

HRID 57643Notes

Reaction equation

HRID 57643 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[N:23]=[C:22]([NH:24][CH2:25][C@H:26]4[O:31][CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27]4)[C:21]4[C:16](=[N:17][CH:18]=[CH:19][N:20]=4)[CH:15]=3)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.Cl>CC(=O)OCC>[NH:28]1[CH2:29][CH2:30][O:31][C@H:26]([CH2:25][NH:24][C:22]2[C:21]3[C:16](=[N:17][CH:18]=[CH:19][N:20]=3)[CH:15]=[C:14]([C:11]3[CH:10]=[CH:9][C:8]([N:5]4[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]4)=[CH:13][CH:12]=3)[N:23]=2)[CH2:27]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86717400(R)-tert-butyl 2-((7-(4-(4-hydroxypiperidin-1-yl)phenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholine-4-carboxylate

Product 1

HCID 86717401(S)-1-(4-(5-(morpholin-2-ylmethylamino)pyrido[4,3-b]pyrazin-7-yl)phenyl)piperidin-4-olYield 45.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

(R)-tert-butyl 2-((7-(4-(4-hydroxypiperidin-1-yl)phenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholine-4-carboxylate (112 mg, 0.21 mmol) was dissolved in 20 mL EA, then 15 mL 5M HCl in EA was added in. The mixture was stirred at room temperature overnight, concentrated, treated with ammonia, purified by preparative TLC to give 40 mg reddish solid. MS: (m/z): 421 (M+H)+

Workup

  1. concentrationconcentrated
  2. additiontreated with ammonia
  3. custompurified by preparative TLC

Sources & evidence

ORD record
ord-35ba6ce6decb45c7869092108a8f920f
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

Loading…