Trifluoroacetic acid → HCID 49838384, compound

HRID 2167647Notes

Reaction equation

HRID 2167647 reaction equation
[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][C:8]([CH2:12][CH2:13][C:14]3[CH:39]=[CH:38][C:17]([O:18][CH2:19][C:20]4[CH:25]=[CH:24][C:23]([CH2:26][C:27]([P:30](=[O:37])([O:34]CC)[O:31]CC)([F:29])[F:28])=[CH:22][CH:21]=4)=[CH:16][C:15]=3[CH3:40])=[CH:7][C:6]=2[C:5]2[CH:41]=[CH:42][C:43]([CH3:45])=[CH:44][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:39]=[CH:38][C:17]([O:18][CH2:19][C:20]4[CH:21]=[CH:22][C:23]([CH2:26][C:27]([P:30](=[O:31])([OH:34])[OH:37])([F:28])[F:29])=[CH:24][CH:25]=4)=[CH:16][C:15]=3[CH3:40])=[CH:7][C:6]=2[C:5]2[CH:41]=[CH:42][C:43]([CH3:45])=[CH:44][C:4]=2[N:3]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86651450HCID 86651450, compound

Product 1

HCID 49838384HCID 49838384, compound

Procedure

2-(4-((4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)methyl)phenyl)-1,1-difluoroethylphosphonic acid (8) was prepared according to the procedure described in Example 1—Step 3, but using diethyl 2-(4-((4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)methyl)phenyl)-1,1-difluoroethylphosphonate from the previous step 3. TFA was added to the 1H NMR sample to solubilize the compound for analysis. The 1H NMR (Dimethylsulfoxide-d6) obtained for 2-(4-((4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)methyl)phenyl)-1,1-difluoroethylphosphonic acid (8) was: δ 9.71 (br, 1H), 9.35 (br, 1H), 9.01 (s, 1H), 8.86 (s, 1H), 8.54 (d, 1H, J=8.4 Hz), 7.53 (s, 1H), 7.44 (d, 1H), 7.40 (s, 1H), 7.38 (s, 1H), 7.29 (d, 1H, J=8.0 Hz), 7.24 (s, 1H), 7.11 (s, 1H), 7.09 (s, 1H), 6.99 (s, 1H), 6.85 (s, 1H), 6.76 (d, 1H, J=8.3 Hz), 5.04 (s, 2H), 3.84-3.73 (m, 2H), 3.15 (t, 2H, J=8.5 Hz), 2.99 (t, 2H, J=8.5 Hz), 2.50 (s, 3H), 2.29 (s, 3H). LRMS [M+H]=578.2

Workup

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

Sources & evidence

ORD record
ord-810ab238631848ba99894e7e35bcc1ca
Source dataset
uspto-grants-2015_06
Patent number
US09045470B2

Reaction notes

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