Diisopropylethylamine → HCID 178499419, compound

HRID 406286Notes

Reaction equation

HRID 406286 reaction equation
[CH3:1][O:2][CH2:3][O:4][CH2:5][C:6]1[N:11]2[CH:12]=[CH:13][N:14]=[C:10]2[C:9]([CH:15]=O)=[CH:8][CH:7]=1.Cl.[Cl:18][C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=1[O:26][C@H:27]1[CH2:30][C@H:29]([NH2:31])[CH2:28]1.CCN(C(C)C)C(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.CO>[Cl:18][C:19]1[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=1[O:26][C@H:27]1[CH2:28][C@H:29]([NH:31][CH2:15][C:9]2[C:10]3[N:11]([CH:12]=[CH:13][N:14]=3)[C:6]([CH2:5][O:4][CH2:3][O:2][CH3:1])=[CH:7][CH:8]=2)[CH2:30]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86710851HCID 86710851, compoundHCID 178479289HCID 178479289, compound

Product 1

HCID 178499419HCID 178499419, compoundYield 29.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of impure 5-({[(methyloxy)methyl]oxy}methyl)imidazo[1,2-a]pyridine-8-carbaldehyde (49 mg, 0.223 mmol) and trans-3-[(2,3-dichlorophenyl)oxy]cyclobutanamine hydrochloride salt (55 mg, 0.205 mmol) in a mixture of DCM (2 mL) and methanol (2 mL) was added DIPEA (0.039 mL, 0.223 mmol) and sodium triacetoxyborohydride (189 mg, 0.89 mmol). The reaction was stirred at ambient temperature for 3.5 hours when LCMS showed the reaction to be complete. DCM (10 mL) was added and the solution washed with saturated aqueous sodium bicarbonate (10 mL). The organic layer was dried (hydrophobic frit) and concentrated in vacuo. The residue was dissolved in DCM and purified on a silica cartridge (20 g) using a 0-10% methanol-DCM gradient over 40 min. The appropriate fractions were combined and evaporated in vacuo to give the title compound as a yellow oil (26 mg).

Workup

  1. customthe reaction
  2. washthe solution washed with saturated aqueous sodium bicarbonate (10 mL)
  3. customThe organic layer was dried (hydrophobic frit)
  4. concentrationconcentrated in vacuo
  5. dissolutionThe residue was dissolved in DCM
  6. custompurified on a silica cartridge (20 g)
  7. customover 40 min
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-6b4feffb50f24020b3997e7931dac2d4
Source dataset
uspto-grants-2014_06
Patent number
US08754101B2

Reaction notes

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