Morpholine → HCID 71512861, compound

HRID 2280980Notes

Reaction equation

HRID 2280980 reaction equation
[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:5]([C:6]([OH:8])=O)=[C:4]([F:13])[CH:3]=1.[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[NH2:1][C:2]1[C:10]([O:11][CH3:12])=[CH:9][C:5]([C:6]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)=[O:8])=[C:4]([F:13])[CH:3]=1

Participants

6

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 529829634-Amino-2-fluoro-5-methoxybenzoic acid

Product 1

HCID 71512861HCID 71512861, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-amino-2-fluoro-5-methoxybenzoic acid (600 mg, 3.24 mmol), morpholine (564 mg, 6.48 mmol), HATU ((O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate, 1.85 g, 4.86 mmol), DIPEA (diisopropyl ethylamine, 836 mg, 6.48 mmol), and CH2Cl2 (20 mL) was stirred at room temperature for 6 h. The solvent was removed under reduced pressure and the residue was purified by silica-gel column chromatography to afford the title compound (560 mg, 68%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by silica-gel column chromatography

Sources & evidence

ORD record
ord-fe50ad8f8dde4440bb2e7ddacff7fff9
Source dataset
uspto-grants-2015_09
Patent number
US09139566B2

Reaction notes

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