Hydrochloric Acid → 4-(pyrrolidin-3-ylmethyl)-3,4-dihydropyrrolo[4,3,2-de][2,6]naphthyridine-5(1H)-one

HRID 1968188Notes

Reaction equation

HRID 1968188 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[CH2:14][CH:15]1[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16]1.Cl>O1CCOCC1>[NH:17]1[CH2:18][CH2:19][CH:15]([CH2:14][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])[CH2:16]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 49841780tert-Butyl 3-((5-oxopyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)methyl)pyrrolidine-1-carboxylate

Product 1

HCID 498417814-(pyrrolidin-3-ylmethyl)-3,4-dihydropyrrolo[4,3,2-de][2,6]naphthyridine-5(1H)-oneYield 104%

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)methyl)pyrrolidine-1-carboxylate (10 mg, 0.03 mmol) in dioxane at 0° C. was added 4N HCl in dioxane (0.019 mL, 0.075 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 (8.0 mg) as its HCl salt. 1H NMR (400 MHz, CD3OD) δ 1.90 (br. s., 1 H) 2.24 (br. s., 1 H) 2.96 (br. s.,1 H) 3.17 (br. s., 2 H) 3.59 (d, J=5.05 Hz, 1 H) 3.71-3.83 (m, 2 H) 3.87 (br. s., 1 H) 5.18 (br. s., 2 H) 7.64 (br. s., 1 H) 7.80 (br. s., 1 H) 8.55 (br. s., 1 H). [M+H] found 257.

Workup

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

Sources & evidence

ORD record
ord-d02fb2d8f4b34f50941dda8d9117f48f
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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