Diisopropylethylamine → (S)-1-(4-(8-bromo-[1,2,4]triazolo[4,3-a]quinoxalin-1-yl)piperidin-1-yl)-2-hydroxypropan-1-one

HRID 711381Notes

Reaction equation

HRID 711381 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]3[N:9]2[C:12]([CH:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[N:13][N:14]=3)=[CH:4][CH:3]=1.[OH:21][C@@H:22]([CH3:26])[C:23](O)=[O:24].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([N:6]=[CH:7][C:8]3[N:9]2[C:12]([CH:15]2[CH2:20][CH2:19][N:18]([C:23](=[O:24])[C@@H:22]([OH:21])[CH3:26])[CH2:17][CH2:16]2)=[N:13][N:14]=3)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 107689L-Lactic AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 668032678-Bromo-1-(piperidin-4-yl)[1,2,4]triazolo[4,3-a]quinoxaline

Product 1

HCID 66803385(S)-1-(4-(8-bromo-[1,2,4]triazolo[4,3-a]quinoxalin-1-yl)piperidin-1-yl)-2-hydroxypropan-1-oneYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 8-bromo-1-(piperidin-4-yl)[1,2,4]triazolo[4,3-a]quinoxaline (250 mg, 0.75 mmol), (S)-2-hydroxypropanoic acid (75 mg, 0.83 mmol), HATU (346 mg, 0.90 mmol), and DIEA (116 mg, 0.90 mmol) in DMF (5 mL) was stirred at r.t. for 6 h. Then the solvents was removed, and the residue was purified by ISCO (MeOH/H2O=20%-90%) to afford (S)-1-(4-(8-bromo-[1,2,4]triazolo[4,3-a]quinoxalin-1-yl)piperidin-1-yl)-2-hydroxypropan-1-one as pale yellow solid (200 mg, yield 66.0%). MS (m/z): 404 (M+H)+.

Workup

  1. customThen the solvents was removed
  2. customthe residue was purified by ISCO (MeOH/H2O=20%-90%)

Sources & evidence

ORD record
ord-55ffa0e944504db493502d1d29f8a0a4
Source dataset
uspto-grants-2015_11
Patent number
US09181264B2

Reaction notes

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