Trifluoroacetic acid → HCID 49838769, 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:36]=[CH:35][C:17]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([P:27](=[O:34])([O:31]CC)[O:28]CC)([F:26])[F:25])=[CH:16][C:15]=3[CH3:37])=[CH:7][C:6]=2[C:5]2[CH:38]=[CH:39][C:40]([CH3:42])=[CH:41][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:36]=[CH:35][C:17]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([P:27](=[O:28])([OH:31])[OH:34])([F:25])[F:26])=[CH:16][C:15]=3[CH3:37])=[CH:7][C:6]=2[C:5]2[CH:38]=[CH:39][C:40]([CH3:42])=[CH:41][C:4]=2[N:3]=1Participants
Procedure
6-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)-1,1-difluorohexylphosphonic acid (24) was prepared according to the procedure described in Example 1—Step 3, but using diethyl 6-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)-1,1-difluorohexylphosphonate from the previous step 2. TFA was added to the 1H NMR sample to solubilize the compound for analysis. The 1H NMR (MeOD-d4) obtained for 6-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)-1,1-difluorohexylphosphonic acid (24) was: δ 8.73 (s, 1H), 8.60 (s, 1H), 8.31 (d, 1H, J=8.4 Hz), 7.48 (s, 1H), 7.43 (d, 1H, J=8.3 Hz), 6.91 (d, 1H, J=8.4 Hz), 6.70 (s, 1H), 6.61 (d, 1H, J=11.0 Hz), 3.90 (t, 2H, J=6.3 Hz), 3.20 (t, 2H, J=7.3 Hz), 3.03 (t, 2H, J=7.5 Hz), 2.54 (s, 2H), 2.22 (s, 3H), 1.79-1.71 (m, 2H), 1.69-1.59 (m, 2H), 1.57-1.47 (m, 2H). LRMS [M+H]=544.2
Workup
- custom6-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)-1,1-difluorohexylphosphonic acid (24) was prepared
Sources & evidence
- ORD record
- ord-a88ae307b74c4cfbb3cf781ed7a1d20c
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09045470B2
Reaction notes
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