Formaldehyde → (4-{[{3-[3-Benzoyl-8-(Trifluoromethyl)Quinolin-4-yl]Phenyl}(Methyl) Amino]Methyl}Phenyl)Acetic Acid

HRID 2104516Notes

Reaction equation

HRID 2104516 reaction equation
[C:1]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[C:19]1[CH:20]=[C:21]([NH:25][CH2:26][C:27]3[CH:32]=[CH:31][C:30]([CH2:33][C:34]([O:36]C)=[O:35])=[CH:29][CH:28]=3)[CH:22]=[CH:23][CH:24]=1)=[CH:16][CH:15]=[CH:14][C:13]=2[C:38]([F:41])([F:40])[F:39])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:42]=O>>[C:1]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:18]=1[C:19]1[CH:20]=[C:21]([N:25]([CH2:26][C:27]3[CH:28]=[CH:29][C:30]([CH2:33][C:34]([OH:36])=[O:35])=[CH:31][CH:32]=3)[CH3:42])[CH:22]=[CH:23][CH:24]=1)=[CH:16][CH:15]=[CH:14][C:13]=2[C:38]([F:39])([F:40])[F:41])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 712FormaldehydeHCID 16718795Methyl {4-[({3-[3-benzoyl-8-(trifluoromethyl)quinolin-4-yl]phenyl}amino)methyl]phenyl}acetate

Product 1

HCID 66914197(4-{[{3-[3-Benzoyl-8-(Trifluoromethyl)Quinolin-4-yl]Phenyl}(Methyl) Amino]Methyl}Phenyl)Acetic Acid

Procedure

The title compound was prepared from methyl {4-[({3-[3-benzoyl-8-(trifluoromethyl)quinolin-4-yl]phenyl}amino)methyl]phenyl}acetate and 37% aqueous formaldehyde followed the procedures of Example 66 as an orange solid MS (EI) m/z 555.3 (M+H)+; 1H NMR (DMSO-d6): δ 2.86 (s, 3H), 3.55 (s, 2H), 4.44 (s, 2H), 6.50 (d, J=7.5 Hz, 1H), 6.60-6.65 (m, 2H), 6.98 (d, J=8.1 Hz, 2H), 7.09 (t, J=7.9 Hz, 1H), 7.18 (d, J=8.0 Hz, 2H), 7.36 (t, J=7.4 Hz, 2H), 7.55 (t, J=6.2 Hz, 1H), 7.64 (d, J=7.0 Hz, 2H), 7.73 (t, J=7.8 Hz, 1H), 8.01 (d, J=7.7 Hz, 1H), 8.30 (d, J=7.0 Hz, 1H), 9.10 (s, 1H), 12.31 (br s, 1H).

Sources & evidence

ORD record
ord-9d48a915aef14e39aeaf016d6a659cb1
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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