Hydrochloric Acid → (S)-2-(methyl(4-(5-(morpholin-2-ylmethylamino)pyrido[4,3-b]pyrazin-7-yl)phenyl)amino)ethanol

HRID 57638Notes

Reaction equation

HRID 57638 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH3:36])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:20]=[C:19]([NH:21][CH2:22][C@H:23]3[O:28][CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24]3)[C:18]3[C:13](=[N:14][CH:15]=[CH:16][N:17]=3)[CH:12]=2)=[CH:7][CH:6]=1.Cl>CC(=O)OCC>[CH3:36][N:4]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:20]=[C:19]([NH:21][CH2:22][C@H:23]3[O:28][CH2:27][CH2:26][NH:25][CH2:24]3)[C:18]3[C:13](=[N:14][CH:15]=[CH:16][N:17]=3)[CH:12]=2)=[CH:9][CH:10]=1)[CH2:3][CH2:2][OH:1]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86717398(R)-tert-butyl 2-((7-(4-((2-hydroxyethyl)(methyl)amino)phenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholine-4-carboxylate

Product 1

HCID 86717399(S)-2-(methyl(4-(5-(morpholin-2-ylmethylamino)pyrido[4,3-b]pyrazin-7-yl)phenyl)amino)ethanol

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

(R)-tert-butyl 2-((7-(4-((2-hydroxyethyl)(methyl)amino)phenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholine-4-carboxylate was dissolved in EA (20 mL), 5M HCl in EA (10 mL) was added, the mixture was stirred at room temperature overnight. It was concentrated, treated with NH3.H2O, concentrated, purified by preparative TLC to give 10 mg reddish-brown solid. MS (m/z): 395 (M+H)+

Workup

  1. concentrationIt was concentrated
  2. additiontreated with NH3.H2O
  3. concentrationconcentrated
  4. custompurified by preparative TLC

Sources & evidence

ORD record
ord-9d041276d94a431385f84fed5828250a
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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