HCID 90416186, compound → HCID 78426332, compound

HRID 1428563Notes

Reaction equation

C([O:8][C:9]1[N:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:22]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([CH2:31][C:32]([CH3:36])([CH3:35])[CH2:33][OH:34])=[C:27]([C:37]([F:40])([F:39])[F:38])[CH:26]=3)=[O:23])=[C:17]([F:41])[CH:16]=2)=[C:11]([O:42][CH2:43][CH3:44])[CH:10]=1)C1C=CC=CC=1>CO.[Pd]>[CH2:43]([O:42][C:11]1[C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][C:22]([NH:24][C:25]3[CH:30]=[CH:29][C:28]([CH2:31][C:32]([CH3:35])([CH3:36])[CH2:33][OH:34])=[C:27]([C:37]([F:39])([F:40])[F:38])[CH:26]=3)=[O:23])=[C:17]([F:41])[CH:16]=2)=[CH:13][NH:14][C:9](=[O:8])[CH:10]=1)[CH3:44]

Participants

Conditions

Temperature: 20 °C

Procedure

The reaction mixture of 2-(4-(6-(benzyloxy)-4-ethoxypyridin-3-yl)-2-fluorophenyl)-N-(4-(3-hydroxy-2,2-dimethylpropyl)-3-(trifluoromethyl)phenyl)acetamide (20 mg, 0.033 mmol) and Pd/C (3.49 mg, 0.033 mmol) in MeOH (3 mL) was stirred at 20° C. for 20 min under a H2 atmosphere. Then the solution was concentrated and purified by preparative HPLC (MeCN/H2O as eluants, acidic condition) to yield a white solid of 2-(4-(4-ethoxy-6-oxo-1,6-dihydropyridin-3-yl)-2-fluorophenyl)-N-(4-(3-hydroxy-2,2-dimethylpropyl)-3-(trifluoromethyl)phenyl)acetamide (11.88 mg, 0.022 mmol, 67.7% yield): 1H NMR (400 MHz, CD3OD) δ 7.95 (d, J=1.98 Hz, 1H), 7.79 (s, 1H), 7.71 (dd, J=8.49, 1.87 Hz, 1H), 7.40-7.46 (m, 2H), 7.25-7.32 (m, 2H), 6.37 (s, 1H), 4.24 (q, J=6.84 Hz, 2H), 3.82 (s, 2H), 3.35 (br. s., 2H), 2.77 (s, 2H), 1.41 (t, J=6.95 Hz, 3H), 0.83 (s, 6H); ES-LCMS m/z 521 (M+H).

Workup

concentrationThen the solution was concentrated
custompurified by preparative HPLC (MeCN/H2O as eluants, acidic condition)

Sources & evidence

ORD record: ord-90eda9c5c5af47e78a6fbd8fe73eec40
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08937071B2

Reaction notes

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