1-{4-[6-(2-Benzyloxy-pyridin-3-yl)-3-phenyl-imidazo[1,2-a]pyridin-2-yl]-phenyl}-cyclobutylamine → HCID 178507126, compound

HRID 872357Notes

Reaction equation

HRID 872357 reaction equation
C([O:8][C:9]1[C:14]([C:15]2[CH:16]=[CH:17][C:18]3[N:19]([C:21]([C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)=[C:22]([C:24]4[CH:29]=[CH:28][C:27]([C:30]5([NH2:34])[CH2:33][CH2:32][CH2:31]5)=[CH:26][CH:25]=4)[N:23]=3)[CH:20]=2)=[CH:13][CH:12]=[CH:11][N:10]=1)C1C=CC=CC=1>CCO>[NH2:34][C:30]1([C:27]2[CH:26]=[CH:25][C:24]([C:22]3[N:23]=[C:18]4[CH:17]=[CH:16][C:15]([C:14]5[C:9]([OH:8])=[N:10][CH:11]=[CH:12][CH:13]=5)=[CH:20][N:19]4[C:21]=3[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:29][CH:28]=2)[CH2:33][CH2:32][CH2:31]1

Participants

3

Reactant 1

HCID 666657401-{4-[6-(2-Benzyloxy-pyridin-3-yl)-3-phenyl-imidazo[1,2-a]pyridin-2-yl]-phenyl}-cyclobutylamine

Product 1

HCID 178507126HCID 178507126, compoundYield 11.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The crude product from Step 3 (167 mg) was dissolved in EtOH (7 mL) whereupon a precipitate formed which was filtered. The filtrate was hydrogenated using an H-Cube flow reactor (Pd/C cartridge, oven temperature 50° C.). The eluant was collected from the flow reactor in two fractions. The second fraction was concentrated in vacuo and triturated with DCM to give a solid which was filtered and dried to give a further portion of title compound (16 mg).

Workup

  1. customformed which
  2. filtrationwas filtered
  3. customan H-Cube flow reactor (Pd/C cartridge, oven temperature 50° C.)
  4. customThe eluant was collected from the flow reactor in two fractions
  5. concentrationThe second fraction was concentrated in vacuo
  6. customtriturated with DCM
  7. customto give a solid which
  8. filtrationwas filtered
  9. customdried

Sources & evidence

ORD record
ord-a3229e01177e486da8142d59db9f0591
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Reaction notes

Loading…