HCID 70976150, compound → HCID 70976021, compound

HRID 455268Notes

Reaction equation

HRID 455268 reaction equation
[N:1]([C@@H:4]1[CH2:23][N:7]2[C:8](=[O:22])[N:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:20])[F:19])=[CH:13][CH:12]=3)[CH2:10][C@@H:6]2[CH2:5]1)=[N+]=[N-]>C1COCC1.[Pd]>[NH2:1][C@@H:4]1[CH2:23][N:7]2[C:8](=[O:22])[N:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]([F:21])([F:19])[F:20])=[CH:13][CH:12]=3)[CH2:10][C@@H:6]2[CH2:5]1

Participants

4

Reactant 1

HCID 70976150HCID 70976150, compound

Product 1

HCID 70976021HCID 70976021, compoundYield 84.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of crude (6S,7aS)-6-Azido-2-(4-trifluoromethoxy-phenyl)-hexahydro-pyrrolo[1,2-c]imidazol-3-one (example 20, step c) (0.90 g) and 10% Pd/C (0.18 g) was stirred in anhydrous THF (20 mL) at the H2 atmosphere for 1 h at 15° C. The mixture was filtered, concentrated and purified by silica gel column chromatography (eluting with DCM/MeOH=50:1˜10:1) to yield 0.70 g of the title compound as a grey solid. 1H NMR (300 MHz, d6-DMSO): δ 7.67 (d, 2H, J=3 Hz), 7.31 (d, 2H, J=9 Hz), 3.96 (d, 1H, J=12 Hz), 3.86 (d, 1H, J=12 Hz), 3.77-3.73 (m, 1H), 3.54-3.52 (m, 1H), 3.18-3.17 (m, 1H), 3.10-3.06 (m, 1H), 2.15-2.11 (m, 1H), 1.69 (s, 2H), 1.35-1.31 (m, 1H); LC-MS: 302.1 [M+1]+.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. custompurified by silica gel column chromatography (eluting with DCM/MeOH=50:1˜10:1)

Sources & evidence

ORD record
ord-22b6481ea35e4caeafe5d033a1ecc800
Source dataset
uspto-grants-2013_07
Patent number
US08497288B2

Reaction notes

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