4-Methylmorpholine → HCID 70098771, compound

HRID 2368379Notes

Reaction equation

HRID 2368379 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([OH:11])=O)=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1.[NH:12]1[CH2:15][CH2:14][CH2:13]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1>C1COCC1>[NH2:1][C:2]1[C:3]([C:9]([N:12]2[CH2:15][CH2:14][CH2:13]2)=[O:11])=[N:4][C:5]([CH3:8])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 10422AzetidineHCID 5726233-Amino-6-methylpicolinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 70098771HCID 70098771, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred mixture of 3-amino-6-methylpicolinic acid (525 mg, 2.17 mmol) and azetidine (124 mg, 146 μl, 2.17 mmol) at r.t. in THF (15 ml) under an argon atmosphere were added HATU (1.65 g, 4.35 mmol) and 4-methylmorpholine (719 μl, 6.52 mmol). The mixture was heated to 70° C. overnight, then cooled to r.t. and concentrated. The crude product was purified by silica gel chromatography using a n-heptane/EtOAc gradient to give the title compound (272 mg, 65%) as off-white solid.

Workup

  1. temperaturecooled to r.t.
  2. concentrationconcentrated
  3. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-bb3545f4adcc4e31a8215083cc83da5f
Source dataset
uspto-grants-2014_04
Patent number
US08703768B2

Reaction notes

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