HCID 67065563, compound → HCID 49838261, compound

HRID 2167643Notes

Reaction equation

HRID 2167643 reaction equation
[P:1]([O:37]CC1C=CC=CC=1)([O:29]CC1C=CC=CC=1)([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[CH:13]=[N:14][C:15]3[C:16]([NH2:27])=[N:17][C:18]4[CH:25]=[C:24]([CH3:26])[CH:23]=[CH:22][C:19]=4[C:20]=3[CH:21]=2)=[C:6]([CH3:28])[CH:5]=1)=[O:2]>CO.[Pd]>[P:1]([OH:29])([OH:37])([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][C:12]2[CH:13]=[N:14][C:15]3[C:16]([NH2:27])=[N:17][C:18]4[CH:25]=[C:24]([CH3:26])[CH:23]=[CH:22][C:19]=4[C:20]=3[CH:21]=2)=[C:6]([CH3:28])[CH:5]=1)=[O:2]

Participants

4

Reactant 1

HCID 67065563HCID 67065563, compound

Product 1

HCID 49838261HCID 49838261, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenyl dibenzyl phosphate (1.0 equiv.) and 10% Pd/C (20% equiv. by weight) in MeOH (0.66 M) was allowed to stir for 18 hours under a balloon of H2. At this point the reaction mixture was passed through a pad of Celite, washing with a 2:1 mixture of CHCl3:MeOH. The combined organic layers were dried over anhydrous Na2SO4 and the volatiles were removed in vacuo. The resulting residue was purified by Reverse Phase-HPLC using a 20-90% 0.5 mM NH4OAc (in MeCN) to 10 mM NH4OAc (in water) gradient to give 4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenyl dihydrogen phosphate (2) as a solid. TFA was added to the 1H NMR sample to solubilize the compound for analysis. 1H NMR (Dimethylsulfoxide-d6): δ 9.69 (br, 1H), 9.33 (s, 1H), 9.03 (s, 1H), 8.87 (s, 1H), 8.54 (d, 1H, J=8.4 Hz), 7.51 (s, 1H), 7.42 (d, 1H, J=9.4 Hz), 7.22 (s, 1H), 7.17 (d, 1H, J=8.3 Hz), 7.10 (s, 1H), 6.97 (s, 1H), 6.92 (d, 1H, J=6.1 Hz), 3.15 (t, 2H, J=6.8 Hz), 3.00 (t, 2H, J=6.8 Hz), 2.50 (s, 3H), 2.29 (s, 3H). LRMS [M+H]=424.1

Workup

  1. washwashing with a 2:1 mixture of CHCl3
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. customthe volatiles were removed in vacuo
  4. customThe resulting residue was purified by Reverse Phase-HPLC

Sources & evidence

ORD record
ord-efa91384c5804882b4499083126a1bea
Source dataset
uspto-grants-2015_06
Patent number
US09045470B2

Reaction notes

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