HCID 86727495, compound → HCID 86727497, compound

HRID 519114Notes

Reaction equation

HRID 519114 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]([CH3:30])([C:12]([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)=[CH2:13])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:11][C:10]([CH3:30])([CH:12]([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)[CH3:13])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 86727495HCID 86727495, compound

Product 1

HCID 86727497HCID 86727497, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-methyl-3-[1-((R)-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl)-vinyl]-azetidine-1-carboxylic acid tert-butyl ester (0.5 g, 1.212 mmol) and Pd/C (0.258 g, 0.242 mmol, 10%) in MeOH (10 mL) was stirred under H2 at ambient temperature for 1 h. The reaction mixture was filtered and the filtrate was evaporated in vacuo to give 3-methyl-3-[1-((R)-4-methyl-3-oxo-2,3,4,10-tetrahydro-9-oxa-1,2,4a-triaza-phenanthren-6-yl)-ethyl]-azetidine-1-carboxylic acid tert-butyl ester (0.484 g, 96%) as a solid. LC/MS (Table 1, Method 25) Rt=0.858 min.; MS m/z: 415 [M+H]+ and 359 [M+H−56]+. 1H NMR (CDCl3, 400 MHz): δ 8.08 (brs, 1H), 6.96 (d, J=8.4 Hz, 1H), 6.83 (d, J=8.4 Hz, 1H), 6.73 (s, 1H), 4.78 (m, 1H), 4.63-4.56 (m, 2H), 3.84 (m, 2H), 3.57 (d, J=8.0 Hz, 1H), 3.35 (d, J=8.0 Hz, 1H), 2.98 (m, 1H), 1.66-1.49 (m, 12H), 1.27 (d, J=7.3 Hz, 3H), 1.21 (s, 3H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated in vacuo

Sources & evidence

ORD record
ord-17dda868138d4f769704b4f358d04d38
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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