Isobutyric Acid → 1-(4-(8-chloro-1H-[1,2,3]triazolo[4,5-c][1,5]naphthyridin-1-yl)piperidin-1-yl)-2-methylpropan-1-one

HRID 711373Notes

Reaction equation

HRID 711373 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]=[N:13][N:14]([CH:15]4[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]4)[C:5]=3[C:4]=2[N:3]=1.[C:21](O)(=[O:25])[CH:22]([CH3:24])[CH3:23].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.O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]=[N:13][N:14]([CH:15]4[CH2:20][CH2:19][N:18]([C:21](=[O:25])[CH:22]([CH3:24])[CH3:23])[CH2:17][CH2:16]4)[C:5]=3[C:4]=2[N:3]=1

Participants

7

Reactant 4

HCID 6590Isobutyric AcidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 866906968-chloro-1-(piperidin-4-yl)-1H-[1,2,3]triazolo[4,5-c][1,5]naphthyridine

Product 1

HCID 866906991-(4-(8-chloro-1H-[1,2,3]triazolo[4,5-c][1,5]naphthyridin-1-yl)piperidin-1-yl)-2-methylpropan-1-oneYield 80.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 8-chloro-1-(piperidin-4-yl)-1H-[1,2,3]triazolo[4,5-c][1,5]naphthyridine (200 mg, 0.69 mmol), isobutyric acid (67 mg, 0.76 mmol), HATU (315 mg, 0.83 mmol) and DIEA (133 mg, 1.04 mmol) in DMF (5 mL) was stirred at r.t. overnight. Then water (10 mL) was added; the precipitate was collected and dried in vacuo to afford 1-(4-(8-chloro-1H-[1,2,3]triazolo[4,5-c][1,5]naphthyridin-1-yl)piperidin-1-yl)-2-methylpropan-1-one as a solid (200 mg).

Workup

  1. customthe precipitate was collected
  2. customdried in vacuo

Sources & evidence

ORD record
ord-178f8b404ec547ce8c1716af39e5e111
Source dataset
uspto-grants-2015_11
Patent number
US09181264B2

Reaction notes

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