Diisopropylethylamine → HCID 49804147, compound

HRID 384972Notes

Reaction equation

HRID 384972 reaction equation
[C@H:1]1([N:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([OH:18])=O)[C:11]2=[O:19])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.CC[N:22]([CH:26]([CH3:28])C)[CH:23]([CH3:25])C.[CH3:29][N:30](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.O>[C@H:1]1([N:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([NH:30][C:29]3[CH:25]=[CH:23][N:22]=[CH:26][CH:28]=3)=[O:18])[C:11]2=[O:19])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66610575(R)-1-(2,3-dihydro-1H-inden-1-yl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid

Product 1

HCID 49804147HCID 49804147, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 7.8 g (1.0 eq.) (R)-1-(2,3-dihydro-1H-inden-1-yl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid in 100 ml DMF was added DIEA (10 ml, 2.5 eq.), HBTU (13.8 g, 1.2 eq.) and 4-amine-pyridin (3.45 g, 1.2 eq.). The resulting mixture was stirred at rt. overnight. The reaction was diluted with 300 ml water. The precipitate was collected by filtration, and washed with 2×50 ml water. The solid was purified on short flash column in silica gel to provide white solid 8.1 g (80%) (R)-1-(2,3-dihydro-1H-inden-1-yl)-2-oxo-N-(pyridin-4-yl)-1,2-dihydropyridine-3-carboxamide. Retention time (min)=2.592, method [7], MS (ESI) 332.1 (M+H); 1H NMR (300 MHz, DMSO-d6) δ 12.99 (s, 1H), 8.72 (d, 2H), 8.49 (d, 1H), 8.19 (d, 2H), 7.68 (d, 1H), 7.36 (m, 2H), 7.33 (m, 1H), 7.24 (m, 1H), 7.15 (d, 1H), 6.61 (t, 1H), 6.49-6.52 (m, 1H), 3.03-3.16 (m, 1H), 2.71-2.98 (m, 1H), 2.66-2.69 (m, 1H), 2.06-2.14 (m, 1H).

Workup

  1. customovernight
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with 2×50 ml water
  4. customThe solid was purified on short flash column in silica gel

Sources & evidence

ORD record
ord-6ab829b45bf8461f8ca73db8b40ea9b2
Source dataset
uspto-grants-2013_02
Patent number
US08367836B2

Reaction notes

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