HCID 86727579, compound → HCID 86727578, compound

HRID 519172Notes

Reaction equation

HRID 519172 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][CH:27]=2)[O:24][CH2:23][C:22]2[N:17]3[C@H:18]([CH3:29])[C:19](=[O:28])[NH:20][N:21]=2)[C@H:10]([CH3:30])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([C:14]2[CH:15]=[C:16]3[C:25](=[CH:26][CH:27]=2)[O:24][CH2:23][C:22]2[N:17]3[C@H:18]([CH3:29])[C:19](=[O:28])[NH:20][N:21]=2)[C@H:10]([CH3:30])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86727579HCID 86727579, compound

Product 1

HCID 86727578HCID 86727578, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (S)-3-methyl-4-((R)-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 (Example #199, Step B, isomer 2, SFC (Table 1, Method 42), Rt=6.856 min., 0.55 g, 1.333 mmol) and 10% Pd/C (0.142 g) in MeOH (20 mL) was stirred at rt for 3 h. The reaction mixture was filtered and the filtrate was concentrated in vacuo to give (3S,4S)-3-methyl-4-((R)-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 (0.55 g, 100%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 8.40 (brs, 1H), 6.98-6.91 (d, J=8.0 Hz, 1H), 6.75-6.70 (d, J=8.0 Hz, 1H), 6.70-6.65 (s, 1H), 4.76-4.70 (q, J=6.8 Hz, 1H), 4.64-4.52 (d, J=13.2 Hz, 2H), 4.47-4.18 (m, 1H), 4.10-3.96 (m, 1H), 3.18-2.66 (m, 3H), 2.10-1.90 (m, 2H), 1.62-1.55 (m, 1H), 1.53-1.45 (m, 12H), 0.70 (d, J=6.8 Hz, 3H). LC/MS (Table 1, Method 25) Rt=0.864 min.; MS m/z: 415 [M+H]+& 359 [M+H−56]+. SFC (Table 1, Method 45), Rt=4.693 min.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-6418c09a8abe4fbaafe124bf9991363c
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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