Nitrogen → HCID 59371503, compound

HRID 2095325Notes

Reaction equation

HRID 2095325 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[C:16]([C:20]2[CH:21]=[C:22]([CH2:26][CH2:27][CH2:28][NH:29]C(=O)OCC3C=CC=CC=3)[CH:23]=[CH:24][CH:25]=2)[CH:17]=[N:18][CH:19]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].N#N>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12][O:13][C:14]1[CH:15]=[C:16]([C:20]2[CH:21]=[C:22]([CH2:26][CH2:27][CH2:28][NH2:29])[CH:23]=[CH:24][CH:25]=2)[CH:17]=[N:18][CH:19]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 947NitrogenHCID 59371370HCID 59371370, compound

Product 1

HCID 59371503HCID 59371503, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl 3-[3-[5-[[1-(tert-butoxycarbonyl)-2(S)-azetidinyl]methoxy]-3-pyridyl]phenyl]propylcarbamate (71.1 mg, 134 μmol) in methanol (3 mL) was added 10% Pd/C (26 mg). The mixture was stirred magnetically under a H2 atmosphere (balloon) at room temperature for 130 min. H2 was replaced by N2, and the catalyst was removed by filtration over a cotton plug. The solution was evaporated and dried (30° C./oil pump vacuum) to yield 47.3 mg (89%) of a colorless film. MS (EI) m/z 397(M+, 4.3%), 341 (4.3%), 311 (17%), 242 (18%), 241 (25%), 198 (10%), 100 (12%), 70 (14%), 57 (100%), 56 (73%).

Workup

  1. customthe catalyst was removed by filtration over a cotton plug
  2. customThe solution was evaporated
  3. customdried (30° C./oil pump vacuum)
  4. customto yield 47.3 mg (89%) of a colorless film

Sources & evidence

ORD record
ord-984cb6fabb62449a91f6a0661db75062
Source dataset
uspto-grants-2013_05
Patent number
US08445684B2

Reaction notes

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