Trifluoroacetic acid → HCID 49838644, compound

HRID 2167672Notes

Reaction equation

HRID 2167672 reaction equation
[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][C:8]([CH2:12][CH2:13][C:14]3[CH:30]=[CH:29][C:17]([O:18][CH2:19][CH2:20][P:21](=[O:28])([O:25]CC)[O:22]CC)=[CH:16][C:15]=3[CH3:31])=[CH:7][C:6]=2[C:5]2[CH:32]=[CH:33][C:34]([CH3:36])=[CH:35][C:4]=2[N:3]=1.C(O)(C(F)(F)F)=O>CS(C)=O>[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][C:8]([CH2:12][CH2:13][C:14]3[CH:30]=[CH:29][C:17]([O:18][CH2:19][CH2:20][P:21](=[O:22])([OH:25])[OH:28])=[CH:16][C:15]=3[CH3:31])=[CH:7][C:6]=2[C:5]2[CH:32]=[CH:33][C:34]([CH3:36])=[CH:35][C:4]=2[N:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86651457HCID 86651457, compound

Product 1

HCID 49838644HCID 49838644, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)ethylphosphonic acid (22) was prepared according to the procedure described in Example 1—Step 3, but using diethyl 2-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)ethylphosphonate from the previous step 2. TFA was added to the 1H NMR sample to solubilize the compound for analysis. The 1H NMR (dimethyl sulfoxide) obtained for 2-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)ethylphosphonic acid (22) was: δ 8.83 (s, 1H), 8.71 (s, 1H), 8.35 (d, 1H, J=8.3 Hz), 7.35 (s, 1H), 7.15 (d, 1H, J=9.6 Hz), 7.08 (d, 1H, J=8.4 Hz), 7.06-7.03 (br, 2H) 6.71 (s, 1H), 6.64 (d, 1H, J=8.1 Hz), 4.09-3.99 (m, 2H), 3.07 (t, 2H, J=6.9), 2.93 (t, 2H, J=6.7), 2.44 (s, 3 H), 2.26 (s, 3H), 1.72-1.62 (m, 2H). LRMS [M+H]=452.2

Workup

  1. custom2-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)ethylphosphonic acid (22) was prepared

Sources & evidence

ORD record
ord-a5117f9ac412491dbb6248fe3581b42e
Source dataset
uspto-grants-2015_06
Patent number
US09045470B2

Reaction notes

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