(R)-tert-butyl 2-((7-(4-(2-(methylsulfonyl)ethoxy)phenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholine-4-carboxylate → (S)-7-(4-(2-(methylsulfonyl)ethoxy)phenyl)-N-(morpholin-2-yl methyl)pyrido[4,3-b]pyrazin-5-amine

HRID 57645Notes

Reaction equation

[CH3:1][S:2]([CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:23]=[C:22]([NH:24][CH2:25][C@H:26]3[O:31][CH2:30][CH2:29][N:28](C(OC(C)(C)C)=O)[CH2:27]3)[C:21]3[C:16](=[N:17][CH:18]=[CH:19][N:20]=3)[CH:15]=2)=[CH:10][CH:9]=1)(=[O:4])=[O:3]>Cl.CC(=O)OCC>[CH3:1][S:2]([CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[N:23]=[C:22]([NH:24][CH2:25][C@H:26]3[O:31][CH2:30][CH2:29][NH:28][CH2:27]3)[C:21]3[C:16](=[N:17][CH:18]=[CH:19][N:20]=3)[CH:15]=2)=[CH:12][CH:13]=1)(=[O:3])=[O:4]

Participants

Conditions

Temperature: 20 °C

Procedure

(R)-tert-butyl 2-((7-(4-(2-(methylsulfonyl)ethoxy)phenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)morpholine-4-carboxylate (76 mg, 0.14 mmol) was dissolved in a solution of HCl/EA (5 N, 5 mL) and stirred for 4 hours at 20° C. The reaction was concentrated and washed with sat. NaHCO3, water and brine, concentrated and purified on TLC (CH2Cl2:MeOH=5:1) to give yellow solid. MS (m/z): 444 (M+H)+

Workup

concentrationThe reaction was concentrated
washwashed with sat. NaHCO3, water and brine
concentrationconcentrated
custompurified on TLC (CH2Cl2:MeOH=5:1)
customto give yellow solid

Sources & evidence

ORD record: ord-1399d028913f41bd870728c6b0c1e792
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434726B2

Reaction notes

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