Trifluoroacetic acid → HCID 49838133, compound
Reaction equation
[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][C:8]([CH2:12][CH2:13][C:14]3[CH:34]=[CH:33][C:17]([O:18][CH2:19][CH2:20][CH2:21][C:22]([P:25](=[O:32])([O:29]CC)[O:26]CC)([F:24])[F:23])=[CH:16][C:15]=3[CH3:35])=[CH:7][C:6]=2[C:5]2[CH:36]=[CH:37][C:38]([CH3:40])=[CH:39][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:34]=[CH:33][C:17]([O:18][CH2:19][CH2:20][CH2:21][C:22]([P:25](=[O:26])([OH:29])[OH:32])([F:23])[F:24])=[CH:16][C:15]=3[CH3:35])=[CH:7][C:6]=2[C:5]2[CH:36]=[CH:37][C:38]([CH3:40])=[CH:39][C:4]=2[N:3]=1Participants
Procedure
4-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)-1,1-difluorobutylphosphonic acid (5) was prepared according to the procedure described in Example 1—Step 3, but using diethyl 4-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)-1,1-difluorobutylphosphonate from step 2. TFA was added to the 1H NMR sample to solubilize the compound for analysis. The 1H NMR (Dimethylsulfoxide-d6) obtained for 4-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)-1,1-difluorobutylphosphonic acid (5) was: δ 9.71 (br, 1H), 9.33 (br, 1H), 9.00 (s, 1H), 8.85 (s, 1H), 8.54 (d, 1H, J=8.4 Hz), 7.53 (s, 1H), 7.42 (d, 1H, J=8.3 Hz), 7.08 (d, 1H, J=8.4 Hz), 6.76 (s, 1H), 6.70 (d, 1H, J=8.3 Hz), 3.97 (t, 2H, J=6.2 Hz), 3.15 (t, 2H, J=8.5 Hz), 2.98 (t, 2H, J=8.5 Hz), 2.50 (s, 3H), 2.28 (s, 3H), 2.21-2.06 (m, 2H), 1.97-1.87 (m, 2H). LRMS [M+H]=516.2
Workup
- custom4-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)-1,1-difluorobutylphosphonic acid (5) was prepared
Sources & evidence
- ORD record
- ord-ac7c802a56b4459d8680e1842958297d
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09045470B2
Reaction notes
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