4-Methylmorpholine → HCID 71288488, compound

HRID 1621085Notes

Reaction equation

HRID 1621085 reaction equation
Cl.Cl.[N:3]1[C:4]([CH2:12][CH2:13][NH2:14])=[CH:5][N:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=12.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=C[C:25]=2[N:24]=[N:23]1.C[N:40]1[CH2:45][CH2:44]OC[CH2:41]1.C([O:49][CH2:50][CH3:51])(=O)C.[CH3:52]O.C([O:57][CH2:58][CH3:59])(=O)C>C1COCC1>[N:3]1[C:4]([CH2:12][CH2:13][NH:14][C:58]([C:59]2[N:24]([CH3:25])[N:23]=[CH:52][C:51]=2[C:50]([N:40]2[CH2:41][CH2:44][CH2:45]2)=[O:49])=[O:57])=[CH:5][N:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=12

Participants

7

Reactant 5

HCID 79724-MethylmorpholineHCID 8857Ethyl AcetateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21522443HCID 21522443, compoundHCID 21584119Ethylacetate methanol

Product 1

HCID 71288488HCID 71288488, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of intermediate A-1 (32 mg, 153 μmol), 2-(imidazo[1,2-a]pyridin-2-yl)ethanamine dihydrochloride (46.7 mg, 199 μmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU; 64.1 mg, 169 μmol) and N-methylmorpholine (84.3 μL, 767 μmol) in THF (1.5 mL) was heated under nitrogen atmosphere at 70° C. for 16 hr. The reaction mixture was cooled to RT, poured into ethyl acetate (50 mL) and extracted with water (2×15 mL). The organic phase was washed with brine (15 mL) and the aqueous layers were back-extracted with ethyl acetate (1×50 mL). The organic layers were dried over MgSO4 and concentrated in vacuo. The crude material was purified by flash chromatography (using silica gel and a MeOH/ethyl acetate gradient) to give the title compound (18 mg, 51.1 μmol, 33.3%) as colorless solid. MS: M=353.2 (M+H)+

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. extractionextracted with water (2×15 mL)
  3. washThe organic phase was washed with brine (15 mL)
  4. extractionthe aqueous layers were back-extracted with ethyl acetate (1×50 mL)
  5. dry with materialThe organic layers were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude material was purified by flash chromatography (

Sources & evidence

ORD record
ord-b2108f07e87c455eac026456e559fc07
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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