3-(Acetylamino)-4-(2-methylpiperidin-1-yl)benzoic acid → Methyl 4-{5-[3-(acetylamino)-4-(2-methylpiperidin-1-yl)phenyl]-1,2,4-oxadiazol-3-yl}-2-fluorobenzoate

HRID 219939Notes

Reaction equation

HRID 219939 reaction equation
[NH2:1][C:2](=[N:14][OH:15])[C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([F:13])[CH:4]=1.[C:16]([NH:19][C:20]1[CH:21]=[C:22]([CH:26]=[CH:27][C:28]=1[N:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]1[CH3:35])[C:23](O)=O)(=[O:18])[CH3:17]>CO>[C:16]([NH:19][C:20]1[CH:21]=[C:22]([C:23]2[O:15][N:14]=[C:2]([C:3]3[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([F:13])[CH:4]=3)[N:1]=2)[CH:26]=[CH:27][C:28]=1[N:29]1[CH2:34][CH2:33][CH2:32][CH2:31][CH:30]1[CH3:35])(=[O:18])[CH3:17]

Participants

4

Reactant 2

HCID 594958243-(Acetylamino)-4-(2-methylpiperidin-1-yl)benzoic acidHCID 76644654Methyl 4-[amino(hydroxyimino)methyl]-2-fluorobenzoate

Product 1

HCID 67528808Methyl 4-{5-[3-(acetylamino)-4-(2-methylpiperidin-1-yl)phenyl]-1,2,4-oxadiazol-3-yl}-2-fluorobenzoate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound was obtained following procedure described for example 4, step 1, but starting from Intermediate 1 (70 mg; 0.33 mmol) and Intermediate 32 (91.17 mg; 0.33 mmol). Title compound was isolated after trituration with MeOH as an off-white powder. 1H NMR (DMSO-d6, 300 MHz) δ 9.10 (bs, 1H), 8.88, (bs, 1H), 8.11 (t, J=7.6 Hz, 1H), 8.03 (dd, J=8.1, 1.5 Hz, 1H), 7.97-7.87 (m, 2H), 7.45 (d, 8.4 Hz, 1H), 3.90 (s, 3H), 3.19-3.12 (m, 1H), 2.96-2.89 (m, 1H), 2.65-2.57 (m, 1H), 2.19 (s, 3H), 1.87-1.66 (m, 4H), 1.53-1.44 (m, 2H), 0.84 (d, J=6 Hz, 3H). LC/MS (Method B): 453.3 (M+H)+. HPLC (Method A) Rt 5.16 min (purity: 97.5%).

Sources & evidence

ORD record
ord-f0093e66595e42fea10571c1b8e55bf1
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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