HCID 178514593, compound → HCID 178511293, compound

HRID 2373902Notes

Reaction equation

HRID 2373902 reaction equation
[N:1]([CH2:4][C@@H:5]1[CH2:8][C@H:7]([C:9]2[N:13]3[CH:14]=[CH:15][N:16]=[C:17]([NH2:18])[C:12]3=[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH:20]=3)[N:10]=2)[CH2:6]1)=[N+]=[N-]>C(O)C.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[NH2:1][CH2:4][C@@H:5]1[CH2:6][C@H:7]([C:9]2[N:13]3[CH:14]=[CH:15][N:16]=[C:17]([NH2:18])[C:12]3=[C:11]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH:20]=3)[N:10]=2)[CH2:8]1

Participants

4

Reactant 1

HCID 178514593HCID 178514593, compound

Product 1

HCID 178511293HCID 178511293, compound

Reagents, catalysts & solvents 2

HCID 131709914Lindlars catalystCatalystHCID 702EthanolSolvent

Procedure

cis-3-(3-Azidomethyl-cyclobutyl)-1-(3-benzyloxyphenyl)-imidazo[1,5-a]pyrazin-8-ylamine (35 mg, 0.082 mmol) was dissolved in ethanol (5 mL) upon heating, the mixture was cooled to rt. and charged with Lindlar catalyst (30 mg). The mixture was hydrogenated at rt overnight. LC-MS showed the reaction was complete and clean. The catalyst was removed by filtration through a pad of celite, the filtrate was concentrated and the residue was purified by mass-directed purification to give a white solid; LC-MS (ES, Pos.): m/z 400 [MH+]; 1H NMR (CD3OD, 400 MHz) δ 2.17-2.24 (m, 2H), 2.56-2.67 (m, 3H), 2.79 (d, J=6.5 Hz, 2H), 3.84 (m, 1H), 5.17 (s, 2H), 6.98 (d, J=5.1 Hz, 1H), 7.15-7.47 (m, 10H).

Workup

  1. temperatureupon heating
  2. customThe catalyst was removed by filtration through a pad of celite
  3. concentrationthe filtrate was concentrated
  4. customthe residue was purified by mass-directed purification
  5. customto give a white solid

Sources & evidence

ORD record
ord-d68333d8284a49ea9ca9dd08d199a684
Source dataset
uspto-grants-2008_12
Patent number
US07459554B2

Reaction notes

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