Hydrochloric Acid → 8-{5-[4-(Trifluoromethyl)phenyl]oxazol-2-ylamino}-3,4-dihydronaphthalen-2(1H)-one

HRID 1785537Notes

Reaction equation

C([O:3][C:4]1[CH2:13][C:12]2[C:11]([NH:14][C:15]3[O:16][C:17]([C:20]4[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][CH:21]=4)=[CH:18][N:19]=3)=[CH:10][CH:9]=[CH:8][C:7]=2[CH2:6][CH:5]=1)C.Cl.C([O-])(O)=O.[Na+]>O1CCCC1>[F:29][C:26]([F:27])([F:28])[C:23]1[CH:24]=[CH:25][C:20]([C:17]2[O:16][C:15]([NH:14][C:11]3[CH:10]=[CH:9][CH:8]=[C:7]4[C:12]=3[CH2:13][C:4](=[O:3])[CH2:5][CH2:6]4)=[N:19][CH:18]=2)=[CH:21][CH:22]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of the product of Example 1H (150 mg, 0.375 mmol) in tetrahydrofuran (2.3 mL) was treated with 2N HCl (0.76 mL, 1.52 mmol), and the mixture was heated at 40° C. for 1 hour. After cooling to room temperature, the solution was brought to pH 8 with saturated NaHCO3 solution, and extracted with ethyl acetate. The organic extracts were washed with H2O, dried over Na2SO4, filtered and evaporated in vacuo to the title compound as a brown residue (140 mg, 100%). 1H NMR (DMSO-d6) δ 9.56 (s, 1H), 7.78 (m, 4H), 7.67 (d, 1H, J=7.8 Hz), 7.62 (s, 1H), 7.22 (t, 1H, J=7.8 Hz), 7.06 (d, 1H, J=7.4 Hz), 3.58 (s, 2H), 3.36 (m, 2H), 3.06 (t, 2H, J=6.8 Hz); MS (ESI+) m/z 373 (M+H)+.

Workup

temperatureAfter cooling to room temperature
extractionextracted with ethyl acetate
washThe organic extracts were washed with H2O
dry with materialdried over Na2SO4
filtrationfiltered
customevaporated in vacuo to the title compound as a brown residue (140 mg, 100%)

Sources & evidence

ORD record: ord-7680cbe7cf2148f68c697c57fd8860cb
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07504520B2

Reaction notes

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