Pyridine → tert-Butyl 4-(5-oxopyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)piperidine-1-carboxylate

HRID 1968172Notes

Reaction equation

HRID 1968172 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH2:15][C:16]2[C:24]3[C:23]([C:25](O)=[O:26])=[CH:22][CH:21]=[N:20][C:19]=3[NH:18][CH:17]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.N1C=CC=CC=1>CN(C=O)C>[O:26]=[C:25]1[C:23]2[CH:22]=[CH:21][N:20]=[C:19]3[NH:18][CH:17]=[C:16]([C:24]=23)[CH2:15][N:14]1[CH:11]1[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 672237563-((1-(tert-butoxycarbonyl)piperidin-4-ylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid

Product 1

HCID 49841655tert-Butyl 4-(5-oxopyrrolo[4,3,2-de][2,6]naphthyridin-4(1H,3H,5H)-yl)piperidine-1-carboxylateYield 54.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-((1-(tert-Butoxycarbonyl)piperidin-4-ylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid (35 mg, 0.093 mmol), HATU (71 mg, 0.187 mmol), and pyridine (0.023 mL, 0.280 mmol) were stirred in DMF (3 mL) at room temperature for 2 h. The solution was concentrated in vacuo and purified via basic prep HPLC eluting with 10% to 35% B in A and gave 18 mg of the title compound as a yellow solid. 1H NMR (400 MHz, CD3OD) δ 7.59 (m, 1H), 7.39-7.49 (m, 1H), 4.98 (d, 2H, J=1.5 Hz), 4.77-4.79 (m, 1H), 4.25-4.28 (m, 2H), 2.87-2.92 (m, 2H), 1.91-1.94 (m, 2H), 1.78-1.90 (m, 2H), 1.48 (s, 9H). [M+H] found 357.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. custompurified via basic prep HPLC
  3. washeluting with 10% to 35% B in A

Sources & evidence

ORD record
ord-426086039458485abeb90bc8795095f7
Source dataset
uspto-grants-2013_04
Patent number
US08420816B2

Reaction notes

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