Morpholine → (6-Aminopyridin-3-yl)(morpholino)methanone

HRID 1021622Notes

Reaction equation

HRID 1021622 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:28][C:29]1[CH:37]=[CH:36][C:32]([C:33](O)=[O:34])=[CH:31][N:30]=1>CCO>[NH2:28][C:29]1[N:30]=[CH:31][C:32]([C:33]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[O:34])=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 184966-Aminonicotinic acidHCID 757711-Hydroxybenzotriazole

Product 1

HCID 59259223(6-Aminopyridin-3-yl)(morpholino)methanoneYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of morpholine (9.00 g, 103 mmol) in EtOH (400 mL) was added EDCI (10.0 g, 52.2 mmol), HOBt (7.00 g 51.8 mmol), and 6-aminonicotinic acid (6.00 g, 43.4 mmol). After stirring for 18 h, the resulting suspension was filtered. The solid was triturated with a mixture of MeOH (100 mL) and methylene chloride (100 mL) to afford 111a as a white solid (2.7 g, 30%). LCMS: (M+H)+ 208

Workup

  1. filtrationthe resulting suspension was filtered
  2. customThe solid was triturated with a mixture of MeOH (100 mL) and methylene chloride (100 mL)

Sources & evidence

ORD record
ord-895cf3a8543d4b5bbe22064cf469ce14
Source dataset
uspto-grants-2014_05
Patent number
US08716274B2

Reaction notes

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