Propionic Acid → 4-(4-ethyl-1-propionylpiperidin-4-yl)-3,4-dihydropyrrolo[4,3,2-de][2,6]naphthyridin-5(1H)-one

HRID 1968193Notes

Reaction equation

HRID 1968193 reaction equation
[CH2:1]([C:3]1([N:9]2[CH2:18][C:17]3=[CH:19][NH:20][C:15]4[C:16]3=[C:11]([CH:12]=[CH:13][N:14]=4)[C:10]2=[O:21])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1)[CH3:2].[C:22](O)(=[O:25])[CH2:23][CH3:24].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C)C1C=CN=CC=1.CN(C=O)C>[CH2:1]([C:3]1([N:9]2[CH2:18][C:17]3=[CH:19][NH:20][C:15]4[C:16]3=[C:11]([CH:12]=[CH:13][N:14]=4)[C:10]2=[O:21])[CH2:8][CH2:7][N:6]([C:22](=[O:25])[CH2:23][CH3:24])[CH2:5][CH2:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 1032Propionic AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 49841776HCID 49841776, compound

Product 1

HCID 498419014-(4-ethyl-1-propionylpiperidin-4-yl)-3,4-dihydropyrrolo[4,3,2-de][2,6]naphthyridin-5(1H)-oneYield 32.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

4-(4-Ethylpiperidin-4-yl)-3,4-dihydropyrrolo[4,3,2-de][2,6]naphthyridin-5(1H)-one (12 mg, 0.042 mmol), propionic acid (4 mg, 0.055 mmol), 4-dimethylaminopyridine (10 mg, 0.084 mmol), and HATU (32 mg, 0.084 mmol) were dissolved in DMF (3 mL) at room temperature and allowed to stir for 3 h. The solution was concentrated in vacuo and purified via preparative HPLC 10% to 40% B in A and gave 4.6 mg of the title compound as its TFA salt. 1H NMR (400 MHz, CD3OD) δ 7.58 (m, 1H), 7.41 (m, 1H), 5.12 (s, 2H), 3.70-3.74 (m, 1H), 3.59-3.63 (m, 3H), 2.58-2.61 (m, 1H), 2.41-2.43 (m, 3H), 2.21-2.30 (m, 4H), 1.11 (t, 3H, J=7.6 Hz), 0.94 (t, 3H, J=7.6 Hz). [M+H] found 341.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. custompurified via preparative HPLC 10% to 40% B in A

Sources & evidence

ORD record
ord-6da7bf4e788d4142a567838e3e189efc
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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