5-Methoxy-o-toluidine → HCID 71241065, compound

HRID 1753775Notes

Reaction equation

HRID 1753775 reaction equation
Cl[C:2]1[O:3][C:4]([C:7]2[CH:8]=[C:9]([N:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]3=[O:19])[CH:10]=[N:11][CH:12]=2)=[CH:5][N:6]=1.[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([CH3:29])=[C:26]([CH:28]=1)[NH2:27]>CC(O)C>[CH3:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([CH3:29])=[C:26]([NH:27][C:2]2[O:3][C:4]([C:7]3[CH:8]=[C:9]([N:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]4=[O:19])[CH:10]=[N:11][CH:12]=3)=[CH:5][N:6]=2)[CH:28]=1

Participants

4

Reactant 2

HCID 995005-Methoxy-o-toluidineHCID 71240944HCID 71240944, compound

Product 1

HCID 71241065HCID 71241065, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

5′-[2-(5-Methoxy-2-methyl-phenylamino)-oxazol-5-yl]-[1,3′]bipyridinyl-2-one 221 was prepared as described for I-f above from 5′-(2-Chloro-oxazol-5-yl)-[1,3′]bipyridinyl-2-one VIII-c (68 mg, 0.250 mmol), and 5-methoxy-2-methylaniline (35 mg, 0.250 mmol) in iPrOH (3 mL) to afford the title compound 221 after column chromatography (SiO2; eluting with 2% to 5% EtOH in DCM) as an orange solid (28 mg, 30%). (300 MHz, CDCl3) δ 8.83 (d, J=1.9 Hz, 1H), 8.45 (d, J=2.3 Hz, 1H), 7.93 (t, J=2.1 Hz, 1H), 7.73 (d, J=2.4 Hz, 1H), 7.41 (m, 1H), 7.34 (m, 1H), 7.30 (s, 1H), 7.07 (d, J=8.3 Hz, 1H), 6.78 (s, 1H), 6.68 (d, J=9.3 Hz, 1H), 6.55 (dd, J=8.3, 2.5 Hz, 1H), 6.30 (t, J=5.6 Hz, 1H), 3.81 (s, 3H), 2.25 (s, 3H). ESL MS m/z 375 (M+H)+. Retention time=2.99 min (method 1).

Workup

  1. custom5′-[2-(5-Methoxy-2-methyl-phenylamino)-oxazol-5-yl]-[1,3′]bipyridinyl-2-one 221 was prepared

Sources & evidence

ORD record
ord-7e6c14145bf04a19a199db5c0270b7a2
Source dataset
uspto-grants-2015_10
Patent number
US09168245B2

Reaction notes

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