Tert-butyl 2-((7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)-1,1-dioxo-thiomorpholine-4-carboxylate → 7-(4-morpholinophenyl)-N-(1,1-dioxo-thiomorpholin-2-ylmethyl)pyrido[4,3-b]pyrazin-5-amine

HRID 57649Notes

Reaction equation

HRID 57649 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:12]=[CH:11][C:10]([C:13]3[N:22]=[C:21]([NH:23][CH2:24][CH:25]4[S:30](=[O:32])(=[O:31])[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26]4)[C:20]4[C:15](=[N:16][CH:17]=[CH:18][N:19]=4)[CH:14]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1>Cl.C(OCC)(=O)C>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:8]=[CH:9][C:10]([C:13]3[N:22]=[C:21]([NH:23][CH2:24][CH:25]4[S:30](=[O:32])(=[O:31])[CH2:29][CH2:28][NH:27][CH2:26]4)[C:20]4[C:15](=[N:16][CH:17]=[CH:18][N:19]=4)[CH:14]=3)=[CH:11][CH:12]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 86717408Tert-butyl 2-((7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)-1,1-dioxo-thiomorpholine-4-carboxylate

Product 1

HCID 867174097-(4-morpholinophenyl)-N-(1,1-dioxo-thiomorpholin-2-ylmethyl)pyrido[4,3-b]pyrazin-5-amineYield 77.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

The tert-butyl 2-((7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)-1,1-dioxo-thiomorpholine-4-carboxylate (52 mg, 0.094 mmol) was dissolved in the solution of HCl in ethyl acetate (3 mL), and the mixture was stirred at room temperature for 2 hours until TLC indicated Boc group was removed. The volatile materials was removed, the residue was neutralized with ammonium hydroxide (25%, 1 mL) and purified by C18 column to afford yellow solid 33 mg. MS (m/z): 455 (M+H)+

Workup

  1. customwas removed
  2. customThe volatile materials was removed
  3. custompurified by C18 column

Sources & evidence

ORD record
ord-1a7876c106914f51b5faabb6ad118692
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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