HCID 86727572, compound → HCID 86727571, compound

HRID 519168Notes

Reaction equation

HRID 519168 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 86727572HCID 86727572, compound

Product 1

HCID 86727571HCID 86727571, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (R)-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 (isomer 1, SFC (Table 1, Method 42), Rt=8.561 min., 0.55 g, 1.333 mmol) and Pd/C (10%, 0.142 g) in MeOH (20 mL) was stirred under an atmosphere of H2 (1 atm) at ambient temperature for 3 h. The reaction mixture was filtered and the filtrate was concentrated in vacuo to give (3R,4R)-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 (0.54 g, 98%) as a colorless solid. 1H NMR (CDCl3, 400 MHz) δ 8.35 (s, 1H), 6.97 (d, J=8.4 Hz, 1H), 6.79 (d, J=8.4 Hz, 1H), 6.71 (s, 1H), 4.77 (q, J=6.8 Hz, 1H), 4.65-4.52 (d, J=13.2 Hz, 2H), 4.48-3.98 (m, 2H), 3.18-2.73 (m, 3H), 2.13-1.92 (m, 2H), 1.61 (brs, 1H), 1.55-1.48 (m, 13H), 0.76-0.67 (d, J=5.6 Hz, 3H). LC/MS (Table 1, Method 25), Rt=0.869 min.; MS m/z: 415 [M+H]+. SFC (Table 1, Method 45), Rt=4.910 min.

Workup

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

Sources & evidence

ORD record
ord-e1b957b8707944c68790dc4724342939
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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