4-Methylmorpholine → HCID 70098771, compound

HRID 467782Notes

Reaction equation

HRID 467782 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-64e5273824cf4e76a7c57ea0b551d7c5
Source dataset
uspto-grants-2014_01
Patent number
US08623866B2

Reaction notes

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