Morpholine → 3-(4-Morpholinylmethyl)-7-(4-phenyl-1-piperidinyl)-1,2,4-triazolo[4,3-a]pyridine-8-carbonitrile

HRID 1428517Notes

Reaction equation

HRID 1428517 reaction equation
[C:1]([C:3]1[C:4]2[N:5]([C:21]([CH:24]=O)=[N:22][N:23]=2)[CH:6]=[CH:7][C:8]=1[N:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)#[N:2].[NH:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[N:26]1([CH2:24][C:21]2[N:5]3[CH:6]=[CH:7][C:8]([N:9]4[CH2:14][CH2:13][CH:12]([C:15]5[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=5)[CH2:11][CH2:10]4)=[C:3]([C:1]#[N:2])[C:4]3=[N:23][N:22]=2)[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 574595958-Cyano-3-formyl-7-(4phenylpiperidinyl)[1,2,4]triazolo[4,3-a]pyridine

Product 1

HCID 667887433-(4-Morpholinylmethyl)-7-(4-phenyl-1-piperidinyl)-1,2,4-triazolo[4,3-a]pyridine-8-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of D9 (0.065 g, 0.196 mmol) in DCM (2.5 ml) were added morpholine (0.026 g, 0.294 mmol) and sodium triacetoxy-borohydride (0.062 mg, 0.294 mmol). The resulting mixture was stirred at r.t. for 1 day. The reaction mixture was washed with H2O, dried (MgSO4) and concentrated in vacuo. The crude product thus obtained was purified by column chromatography (silica gel; DCM/MeOH up to 3% as eluent). The desired fractions were collected and concentrated in vacuo to yield final compound E11 (0.04 g, 51%) as a white solid.

Workup

  1. washThe reaction mixture was washed with H2O
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude product thus obtained
  5. customwas purified by column chromatography (silica gel; DCM/MeOH up to 3% as eluent)
  6. customThe desired fractions were collected
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-120ab1f3384a4aa2b21fe3751293b0cd
Source dataset
uspto-grants-2015_01
Patent number
US08937060B2

Reaction notes

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