Trifluoroacetic acid → 3-(4-(2-(5-Amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)propylphosphonic acid
Reaction equation
[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][C:8]([CH2:12][CH2:13][C:14]3[CH:31]=[CH:30][C:17]([O:18][CH2:19][CH2:20][CH2:21][P:22](=[O:29])([O:26]CC)[O:23]CC)=[CH:16][C:15]=3[CH3:32])=[CH:7][C:6]=2[C:5]2[CH:33]=[CH:34][C:35]([CH3:37])=[CH:36][C:4]=2[N:3]=1.C(O)(C(F)(F)F)=O>>[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][C:8]([CH2:12][CH2:13][C:14]3[CH:31]=[CH:30][C:17]([O:18][CH2:19][CH2:20][CH2:21][P:22](=[O:23])([OH:26])[OH:29])=[CH:16][C:15]=3[CH3:32])=[CH:7][C:6]=2[C:5]2[CH:33]=[CH:34][C:35]([CH3:37])=[CH:36][C:4]=2[N:3]=1Participants
Procedure
3-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)propylphosphonic acid (1) was prepared according to the procedure described in Example 1—Step 3, but using diethyl 3-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)propylphosphonate from the previous step. TFA was added to the 1H NMR sample to solubilize the compound for analysis. The 1H NMR (Dimethylsulfoxide-d6) obtained for 3-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)propylphosphonic acid (1) was: δ 9.72 (br, 1H), 9.01 (s, 1H), 8.96 (br, 1H), 8.85 (s, 1H), 8.54 (d, 1H, J=8.4 Hz), 7.54 (s, 1H), 7.42 (d, 1H, J=8.2 Hz), 7.08 (d, 1H, J=8.4 Hz), 6.74 (s, 1H), 6.66 (d, 1H, J=8.3 Hz), 3.95 (t, 2H, J=6.4 Hz), 3.14 (t, 2H, J=8.6 Hz), 2.97 (t, 2H, J=8.6 Hz), 2.50 (s, 3H), 2.27 (s, 3H), 1.91-1.81 (m, 2H), 1.67-1.56 (m, 2H). LRMS [M+H]=466.2
Workup
- custom3-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)propylphosphonic acid (1) was prepared
Sources & evidence
- ORD record
- ord-70c63b9379554b8789a762cfb210c592
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09045470B2
Reaction notes
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