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

HRID 1968192Notes

Reaction equation

HRID 1968192 reaction equation
[O:1]=[C:2]1[C:11]2[CH:10]=[CH:9][N:8]=[C:7]3[NH:12][CH:13]=[C:5]([C:6]=23)[CH2:4][N:3]1[CH:14]1[CH2:19][CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15]1.Cl>O1CCOCC1>[NH:16]1[CH2:17][CH2:18][CH2:19][CH:14]([N:3]2[CH2:4][C:5]3=[CH:13][NH:12][C:7]4[C:6]3=[C:11]([CH:10]=[CH:9][N:8]=4)[C:2]2=[O:1])[CH2:15]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 49841899tert-butyl 3-(5-oxopyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)piperidine-1-carboxylate

Product 1

HCID 498419004-(piperidin-3-yl)-3,4-dihydropyrrolo[4,3,2-de][2,6]naphthyridin-5(1H)-oneYield 78%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of tert-butyl 3-(5-oxopyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)piperidine-1-carboxylate (10 mg, 0.028 mmol) in dioxane at 0° C. was added 4N HCl in dioxane (0.018 mL, 0.07 mmol) and the reaction mixture was stirred for 1 h to give a solid. The solid was filtered and dried to afford the title compound (5.6 mg) as its HCl salt. 1H NMR (400 MHz, CD3OD) δ 1.82-2.13 (m, 2 H) 2.13-2.31 (m, 2 H) 3.02 (td, J=13.07, 2.91 Hz, 1 H) 3.41 (d, J=1.77 Hz, 1 H) 3.44-3.51 (m, 2 H) 4.68-4.84 (m, 1 H) 5.00-5.19 (m, 2 H) 7.59 (s, 1 H) 7.73 (d, J=6.06 Hz, 1 H) 8.52 (d, J=6.06 Hz, 1 H)). [M+H] found 257.

Workup

  1. customto give a solid
  2. filtrationThe solid was filtered
  3. customdried

Sources & evidence

ORD record
ord-37dbfcc5232f41d1976bc54279bc42d5
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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