Diisopropylethylamine → HCID 178499420, compound

HRID 406287Notes

Reaction equation

HRID 406287 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.[F:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C@H:26]2[CH2:29][C@H:28]([NH2:30])[CH2:27]2)=[CH:21][C:20]=1[C:31]([F:34])([F:33])[F:32].CCN(C(C)C)C(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.CO>[F:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C@H:26]2[CH2:29][C@H:28]([NH:30][CH2:15][C:9]3[C:10]4[N:11]([CH:12]=[CH:13][N:14]=4)[C:6]([CH2:5][O:4][CH2:3][O:2][CH3:1])=[CH:7][CH:8]=3)[CH2:27]2)=[CH:21][C:20]=1[C:31]([F:32])([F:33])[F:34]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86710851HCID 86710851, compoundHCID 178479290HCID 178479290, compound

Product 1

HCID 178499420HCID 178499420, compoundYield 45.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 5-({[(methyloxy)methyl]oxy}methyl)imidazo[1,2-a]pyridine-8-carbaldehyde (34 mg, 0.154 mmol) and trans-3-{[4-fluoro-3-(trifluoromethyl)phenyl]oxy}cyclobutanamine hydrochloride salt (44 mg, 0.154 mmol) in a mixture of DCM (1 mL) and methanol (1 mL) was added DIPEA (0.027 mL, 0.155 mmol) and sodium triacetoxyborohydride (98 mg, 0.463 mmol). The reaction was stirred at ambient temperature for 3.5 hours and then diluted with DCM (10 mL). The solution was then washed with saturated aqueous sodium bicarbonate (10 mL), dried (hydrophobic frit) and concentrated in vacuo. The residue was dissolved in DCM and purified on a silica cartridge (10 g) using a 0-10% methanol-DCM gradient over 40 min. The product containing fractions were combined and evaporated in vacuo to give the title compound as a yellow oil (32 mg).

Workup

  1. washThe solution was then washed with saturated aqueous sodium bicarbonate (10 mL)
  2. customdried (hydrophobic frit)
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in DCM
  5. custompurified on a silica cartridge (10 g)
  6. customover 40 min
  7. additionThe product containing fractions
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-0cdf1ff18c3d45559a250ade8bd5f6c1
Source dataset
uspto-grants-2014_06
Patent number
US08754101B2

Reaction notes

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