Hydrochloric Acid → 3-{5-[6-(4-methyl-pyridin-2-ylamino)-pyridin-2-yl]-oxazol-2-yl}-1H-pyridin-2-one

HRID 1854616Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of {6-[2-(2-methoxy-pyridin-3-yl)-oxazol-5-yl]-pyridin-2-yl}-(4-methyl-pyridin-2-yl)-amine above (236 mg, 0.655 mmol) in EtOH (10 ml) was treated with conc. HCl (1 ml) and heated to 80° C. for 3 h and then 60° C. for 18 h. The cooled mixture was treated with water and the product precipitated as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 12.23 (s, 1H), 9.78 (s, 1H), 8.29-8.22 (m, 1H), 8.11 (d, J=5.0 Hz, 1H), 7.86 (s, 1H), 7.82-7.73 (m, 2H), 7.69-7.63 (m, 1H), 7.60 (d, J=8.4 Hz, 1H), 7.29 (d, J=7.4 Hz, 1H), 6.77 (d, J=5.0 Hz, 1H), 6.40 (t, J=6.7 Hz, 1H), 2.35 (s, 3H). (ESI+) m/z 346 (M+H)+. Retention time=2.02 mins (method 1).

Workup

customthe product precipitated as a yellow solid

Sources & evidence

ORD record: ord-7dbec72bbcf841eeb1e76b1b8f5cdfcb
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08962665B2

Reaction notes

Loading…