Potassium Carbonate → (1R)-1-[(4-Amino-4-methyl-1-piperidinyl)methyl]-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dione

HRID 1943206Notes

Reaction equation

HRID 1943206 reaction equation
[O:1]=[C:2]1[CH:11]=[CH:10][C:9]2[CH:8]=[CH:7][C:6](=[O:12])[N:5]3[C@H:13]([CH2:15][N:16]4[CH2:21][CH2:20][C:19]([NH:23]C(=O)C(F)(F)F)([CH3:22])[CH2:18][CH2:17]4)[CH2:14][N:3]1[C:4]=23.C(=O)([O-])[O-].[K+].[K+]>>[NH2:23][C:19]1([CH3:22])[CH2:18][CH2:17][N:16]([CH2:15][C@H:13]2[N:5]3[C:4]4[N:3]([C:2](=[O:1])[CH:11]=[CH:10][C:9]=4[CH:8]=[CH:7][C:6]3=[O:12])[CH2:14]2)[CH2:21][CH2:20]1

Participants

3

Reactant 2

HCID 11430Potassium CarbonateHCID 86642105N-(1-{[(1R)-4,9-Dioxo-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridin-1-yl]methyl}-4-methyl-4-piperidinyl)-2,2,2-trifluoroacetamide

Product 1

HCID 68595973(1R)-1-[(4-Amino-4-methyl-1-piperidinyl)methyl]-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridine-4,9-dioneYield 46%

Procedure

N-(1-{[(1R)-4,9-Dioxo-1,2-dihydro-4H,9H-imidazo[1,2,3-ij]-1,8-naphthyridin-1-yl]methyl}-4-methyl-4-piperidinyl)-2,2,2-trifluoroacetamide (171 mg, 0.417 mmol) was treated with a 7% solution of potassium carbonate (450 mg in 2 ml water/5 ml methanol) and stirred at rt for 2 h, and then at 70° C. for 18 h then evaporated and dissolved in 5% MeOH/DCM (100 ml), filtered and purified by SCX (5 g, eluting with MeOH and then 0.5M NH3/MeOH and then 2M NH3/MeOH). Fractions containing product were then evaporated to give product as a pink solid (60 mg, 46%)

Workup

  1. customat 70° C. for 18 h then evaporated
  2. dissolutiondissolved in 5% MeOH/DCM (100 ml)
  3. filtrationfiltered
  4. custompurified by SCX (5 g
  5. washeluting with MeOH
  6. additionFractions containing product
  7. customwere then evaporated

Sources & evidence

ORD record
ord-b8c2159e749145bf8b0e9b31657d9456
Source dataset
uspto-grants-2013_03
Patent number
US08389524B2

Reaction notes

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