Trifluoroacetic acid → HCID 49838263, 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:35]=[CH:34][C:17]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([P:26](=[O:33])([O:30]CC)[O:27]CC)([F:25])[F:24])=[CH:16][C:15]=3[CH3:36])=[CH:7][C:6]=2[C:5]2[CH:37]=[CH:38][C:39]([CH3:41])=[CH:40][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:35]=[CH:34][C:17]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([P:26](=[O:27])([OH:30])[OH:33])([F:24])[F:25])=[CH:16][C:15]=3[CH3:36])=[CH:7][C:6]=2[C:5]2[CH:37]=[CH:38][C:39]([CH3:41])=[CH:40][C:4]=2[N:3]=1Participants
Procedure
5-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)-1,1-difluoropentylphosphonic acid (4) was prepared according to the procedure described in Example 1—Step 3, but using diethyl 5-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)-1,1-difluoropentylphosphonate from step 2. TFA was added to the 1H NMR sample to solubilize the compound for analysis. The 1H NMR (Dimethylsulfoxide-d6) obtained for 5-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)-1,1-difluoropentylphosphonic acid (4) was: δ 9.70 (br, 1H), 9.33 (br, 1H), 8.98 (s, 1H), 8.84 (s, 1H), 8.50 (d, 1H, J=8.4 Hz), 7.52 (s, 1H), 7.40 (d, 1H, J=8.4 Hz), 7.06 (d, 1H, J=8.4 Hz), 6.74 (s, 1H), 6.68 (d, 1H, J=10.8 Hz), 3.91 (t, 2H, J=6.2 Hz), 3.14 (t, 2H, J=8.4 Hz), 2.97 (t, 2H, J=8.4 Hz), 2.50 (s, 3H), 2.27 (s, 3H), 2.13-1.94 (m, 2H), 1.78-1.70 (m, 2H), 1.66-1.59 (m, 2H). LRMS [M+H]=530.2
Workup
- custom5-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)-1,1-difluoropentylphosphonic acid (4) was prepared
Sources & evidence
- ORD record
- ord-5339e065f4b24dcaa395de80fa2fd89e
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09045470B2
Reaction notes
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