HCID 86727588, compound → HCID 86727589, compound

HRID 519179Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH:12]=[C:11]([C:14]2[CH:15]=[C:16]3[C:25](=[CH:26][C:27]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[F:34])[O:24][CH2:23][C:22]2[N:17]3[C@H:18]([CH3:36])[C:19](=[O:35])[NH:20][N:21]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:15]=[C:16]3[C:25](=[CH:26][C:27]=2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=2[F:34])[O:24][CH2:23][C:22]2[N:17]3[C@H:18]([CH3:36])[C:19](=[O:35])[NH:20][N:21]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of Pd/C (10%, 0.324 g, 3.05 mmol) in MeOH (30 mL) was added 4-[(R)-7-(2-fluoro-phenyl)-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl]-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (1.5 g, 3.05 mmol) and the reaction mixture was stirred at 50° C. under H2 (50 psi) overnight. The reaction mixture was cooled to ambient temperature, filtered and the filtrate was concentrated in vacuo to give 4-[(R)-7-(2-fluoro-phenyl)-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl]-piperidine-1-carboxylic acid tert-butyl ester (1.2 g, 80%) as a yellow solid. 1H NMR (400 MHz, methanol-d4) δ 7.49-7.38 (m, 1H), 7.31-7.16 (m, 3H), 7.09 (s, 1H), 6.82 (s, 1H), 5.00-4.94 (m, 1H), 4.68-4.57 (m, 2H), 4.24-4.07 (m, 2H), 2.58 (m, 3H), 1.76 (m, 2H), 1.67-1.56 (m, 2H), 1.50-1.46 (m, 12H).

Workup

temperatureThe reaction mixture was cooled to ambient temperature
filtrationfiltered
concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-36052a847cb24653b0eefb39b7a6155d
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115151B2

Reaction notes

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