Morpholine → HCID 178519298, compound

HRID 2252235Notes

Reaction equation

HRID 2252235 reaction equation
[I:1][C:2]1[C:3]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[C:10]([C:14]([OH:16])=O)[CH:11]=3)[C:4]=2[NH:5][N:6]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.[NH:50]1[CH2:55][CH2:54][O:53][CH2:52][CH2:51]1.C(N(C(C)C)CC)(C)C>CN(C=O)C.CCOC(C)=O>[I:1][C:2]1[C:3]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[C:10]([C:14]([N:50]4[CH2:55][CH2:54][O:53][CH2:52][CH2:51]4)=[O:16])[CH:11]=3)[C:4]=2[NH:5][N:6]=1

Participants

7

Reactant 4

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 2724699PyBOPHCID 178524088HCID 178524088, compound

Product 1

HCID 178519298HCID 178519298, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 84A (0.210 g, 0.644 mmol), PyBOP (0.503 g, 0.966 mmol), morpholine (0.084 mL, 0.966 mmol), and diisopropylethylamine (0.39 mL, 2.25 mmol) in DMF (5 mL) was stirred at room temperature overnight. The reaction mixture was diluted with EtOAc and washed with water and NaHCO3. The organic layer was dried over MgSO4, filtered, concentrated, and purified by flash chromatography eluted with EtOAc to give 0.122 g (48%) of the desired product as red solid. MS (DCI/NH3) m/z: 396.0 (M+H)+; 1H NMR (300 MHz, DMSO-D6) δ ppm 3.46-3.67 (m, 10H) 7.41 (m, 1H) 7.59 (s, brd, 1.5H) 7.67 (d, J=7.46 Hz, 0.5H).

Workup

  1. washwashed with water and NaHCO3
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by flash chromatography
  6. washeluted with EtOAc

Sources & evidence

ORD record
ord-2847e9f2008d4a368a46ed67276649dd
Source dataset
uspto-grants-2008_01
Patent number
US07320986B2

Reaction notes

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