Trifluoroacetic acid → HCID 49838645, compound

HRID 2167673Notes

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][CH2:22][CH2:23][CH2:24][P:25](=[O:32])([O:29]CC)[O:26]CC)=[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][CH2:22][CH2:23][CH2:24][P:25](=[O:26])([OH:29])[OH:32])=[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

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 86651458HCID 86651458, compound

Product 1

HCID 49838645HCID 49838645, compound

Procedure

6-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)hexylphosphonic acid (23) 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)hexylphosphonate. TFA was added to the 1H NMR sample to solubilize the compound for analysis. The 1H NMR (dimethyl sulfoxide-d6) obtained for 6-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)hexylphosphonic acid (23) was: δ 8.95 (s, 1H), 8.81 (s, 1H), 8.50 (d, 1H, J=8.4 Hz), 7.52 (s, 1H), 7.40 (d, 1H, J=8.4 Hz), 7.01 (d, 1H, J=8.4 Hz), 6.71 (s, 1H), 6.64 (d, 1H, J=10.9 Hz), 3.87 (t, 2H, J=6.34 Hz), 3.13 (t, 2H, J=7.1 Hz), 2.96 (t, 2H, J=7.0 Hz), 2.69-2.66 (m, 1H), 2.35-2.32 (m, 1H), 2.25 (s, 2H), 1.72-1.62 (m, 2H), 1.62-1.51 (m, 2H), 1.51-1.40 (m, 2H). LRMS [M+H]=508.2

Workup

custom6-(4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylphenoxy)hexylphosphonic acid (23) was prepared

Sources & evidence

ORD record: ord-d8bdb9645df049918bb727b2fb82be36
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045470B2

Reaction notes

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