Diisopropylethylamine → HCID 44249374, compound

HRID 1987175Notes

Reaction equation

HRID 1987175 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[C@@H:10]([C:11]([OH:13])=O)[CH2:9][N:8]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:7]1)=[O:5])[CH3:2].C(N(CC)C(C)C)(C)C.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.[NH2:45][C:46]1[CH:51]=[CH:50][C:49]([N:52]2[CH:57]=[CH:56][CH:55]=[CH:54][C:53]2=[O:58])=[CH:48][C:47]=1[F:59]>C(#N)C>[CH2:1]([O:3][C:4]([C@@H:6]1[C@@H:10]([C:11](=[O:13])[NH:45][C:46]2[CH:51]=[CH:50][C:49]([N:52]3[CH:57]=[CH:56][CH:55]=[CH:54][C:53]3=[O:58])=[CH:48][C:47]=2[F:59])[CH2:9][N:8]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 221815481-(4-Amino-3-fluorophenyl)pyridin-2-oneHCID 34180170HCID 34180170, compound

Product 1

HCID 44249374HCID 44249374, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

Compound 7a (1.85 g; 6 mmol) is suspended in acetonitrile (20 ml) and N,N-diisopropyl ethyl amin (1.65 ml; 10 mmol) is added at 25° C. BOP-CL (2.46 g; 10 mmol) is added as a solid and after stirring for 30 min at 25° C. 1-(4-amino-3-fluoro-phenyl)-1H-pyridin-2-one (1.45 g; 7 mmol) is added to the reaction mixture. The mixture is stirred for 4 d at 25° C., evaporated to dryness and dissolved in ethyl acetate (200 ml). The organic phase is washed with 2 N HCl (50 ml), with 10% aqueous Na2CO3 solution, water and brine and dried over Na2SO4. The organic phase is filtered and the filtrate is evaporated to dryness. The crude product is purified by silica gel chromatography. Yield: 1.77 g (58.1%), ESI-MS: m/z=472 [M−H]−

Workup

  1. stirringThe mixture is stirred for 4 d at 25° C.
  2. customevaporated to dryness
  3. dissolutiondissolved in ethyl acetate (200 ml)
  4. washThe organic phase is washed with 2 N HCl (50 ml), with 10% aqueous Na2CO3 solution, water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationThe organic phase is filtered
  7. customthe filtrate is evaporated to dryness
  8. customThe crude product is purified by silica gel chromatography

Sources & evidence

ORD record
ord-96509bd7381d43a3a521aa219c227dde
Source dataset
uspto-grants-2009_06
Patent number
US07550487B2

Reaction notes

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