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

HRID 57648Notes

Reaction equation

HRID 57648 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]4S[CH2:29][CH2:28][N:27]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[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.ClC1C=C(C=CC=1)C(OO)=O.[S:49]([O-:53])([O-])(=[O:51])=S.[Na+].[Na+]>C(Cl)Cl>[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:49](=[O:53])(=[O:51])[CH2:29][CH2:28][N:27]([C:31]([O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[O:32])[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

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 71113925Tert-butyl 2-((7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)thiomorpholine-4-carboxylate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-((7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-ylamino)methyl)thiomorpholine-4-carboxylate (178 mg, 0.34 mmol) in CH2Cl2 (5 mL) was added 3-chloroperoxybenzoic acid (70%, 251 mg, 1.02 mmol) at 0° C. The resulting mixture was stirred at room temperature for 3 hours, and subsequently, a saturated aqueous sodium thiosulfate solution was added and the mixture was stirred for another 30 minutes. The layers were separated and the aqueous layer was extracted twice with EtOAc. The combined EtOAc layers were washed twice with an aqueous Na2CO3 solution. The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo to afford title compound 52 mg. MS (m/z): 555 (M+H)+

Workup

  1. stirringthe mixture was stirred for another 30 minutes
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted twice with EtOAc
  4. washThe combined EtOAc layers were washed twice with an aqueous Na2CO3 solution
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0181a6f149ee4b01bf75de11db4c983b
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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