Methanesulfonyl chloride → (S)-(1-(7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-yl)pyrrolidin-3-yl)methyl methanesulfonate

HRID 57618Notes

Reaction equation

HRID 57618 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]([N:23]4[CH2:27][CH2:26][C@H:25]([CH2:28][OH:29])[CH2:24]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.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>C1COCC1>[CH3:30][S:31]([O:29][CH2:28][C@H:25]1[CH2:26][CH2:27][N:23]([C:21]2[C:20]3[C:15](=[N:16][CH:17]=[CH:18][N:19]=3)[CH:14]=[C:13]([C:10]3[CH:11]=[CH:12][C:7]([N:4]4[CH2:3][CH2:2][O:1][CH2:6][CH2:5]4)=[CH:8][CH:9]=3)[N:22]=2)[CH2:24]1)(=[O:33])=[O:32]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 71113365(S)-(1-(7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-yl)pyrrolidin-3-yl)methanol2×

Product 1

HCID 86717384(S)-(1-(7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-yl)pyrrolidin-3-yl)methyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (S)-(1-(7-(4-morpholinophenyl)pyrido[4,3-b]pyrazin-5-yl)pyrrolidin-3-yl)methanol (compound 163, 500 mg, 1.27 mmol) in THF (15 mL) were added MsCl (200 mg, 1.6 mmol) and TEA (370 mg, 3.7 mmol). The mixture was stirred for 4 hours at room temperature and concentrated in vacuo. The residue was washed by H2O and EtOAc to give the title compound. MS (m/z): 470 (M+H)+

Workup

  1. concentrationconcentrated in vacuo
  2. washThe residue was washed by H2O and EtOAc

Sources & evidence

ORD record
ord-5342dae615df4ef996bd43d7b8449c8a
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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