Diisopropylethylamine → 2-(5-methylpyridin-3-yl)-N-(6-(morpholinomethyl)pyridin-2-yl)quinoline-8-carboxamide

HRID 2359436Notes

Reaction equation

HRID 2359436 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[C:11]([C:18]([OH:20])=O)[CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:5]=[N:6][CH:7]=1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[O:54]1[CH2:59][CH2:58][N:57]([CH2:60][C:61]2[N:66]=[C:65]([NH2:67])[CH:64]=[CH:63][CH:62]=2)[CH2:56][CH2:55]1>CN(C=O)C.O>[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[C:11]([C:18]([NH:67][C:65]4[CH:64]=[CH:63][CH:62]=[C:61]([CH2:60][N:57]5[CH2:56][CH2:55][O:54][CH2:59][CH2:58]5)[N:66]=4)=[O:20])[CH:12]=[CH:13][CH:14]=3)[N:9]=2)[CH:5]=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 120778096-(Morpholin-4-ylmethyl)pyridin-2-amineHCID 581546112-(5-Methylpyridin-3-yl)quinoline-8-carboxylic acid

Product 1

HCID 581546572-(5-methylpyridin-3-yl)-N-(6-(morpholinomethyl)pyridin-2-yl)quinoline-8-carboxamideYield 22%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

2-(5-methylpyridin-3-yl)quinoline-8-carboxylic acid (0.135 g, 0.51 mmol) was combined with DIPEA (0.140 mL, 0.811 mmol) and HATU (0.200 g, 0.51 mmol) in DMF (5 mL). The mixture was stirred at room temperature for ten minutes, at which time 6-(morpholinomethyl)pyridin-2-amine (0.090 g, 0.466 mmol) was added. The mixture was stirred 18 hours, and then water (10 mL) was added. The resulting precipitate was collected by filtration, and the solids were triturated in methanol to obtain 2-(5-methylpyridin-3-yl)-N-(6-(morpholinomethyl)pyridin-2-yl)quinoline-8-carboxamide as a tan solid (0.045 g, 22% yield. MS (ESI) calcd for C26H25N5O2 (m/z): 439.20. found: 440 [M+1].

Workup

  1. additionwas added
  2. filtrationThe resulting precipitate was collected by filtration
  3. customthe solids were triturated in methanol

Sources & evidence

ORD record
ord-b3503837a4ce401cb3b63c8de76added
Source dataset
uspto-grants-2014_04
Patent number
US08685970B2

Reaction notes

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