Dimethylformamide → HCID 86673556, compound

HRID 535482Notes

Reaction equation

HRID 535482 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11](=[O:18])[NH:10][N:9]=2)=[CH:4][CH:3]=1.CC([O-])(C)C.[K+].C1(P(O[NH2:40])(C2C=CC=CC=2)=O)C=CC=CC=1.CN(C=O)C>C1COCC1.CCOC(C)=O>[NH2:40][N:10]1[N:9]=[C:8]([C:5]2[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11]1=[O:18]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10955453O-(Diphenylphosphinyl)hydroxylamineHCID 23665647Potassium tert-butoxideHCID 86673555HCID 86673555, compound

Product 1

HCID 86673556HCID 86673556, compoundYield 42.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of the product from Example 4A (0.527 g, 2.04 mmol) and potassium 2-methylpropan-2-olate (0.299 g, 2.66 mmol) in THF (6 mL) was stirred for 1 h, and O-(diphenylphosphoryl)hydroxylamine (0.621 g, 2.66 mmol) and DMF (2 mL) were added, stirred at room temperature for 2 hours, diluted with EtOAc, washed with 1N NaOH and brine, dried (Na2SO4), filtered, and chromatographed (20-60% EtOAc/DCM) to give 235 mg of title compound as a white solid: 1H NMR (300 MHz, DMSO-d6) δ 8.67 (dd, J=2.4, 0.5, 1H), 8.38 (s, 1H), 8.14 (dd, J=8.2, 2.5, 1H), 8.02-7.82 (m, 2H), 7.81-7.65 (m, 2H), 6.54 (s, 2H).

Workup

  1. stirringstirred at room temperature for 2 hours
  2. washwashed with 1N NaOH and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customchromatographed (20-60% EtOAc/DCM)

Sources & evidence

ORD record
ord-76cf0b243fe4400eb8a72cd0e705fea9
Source dataset
uspto-grants-2014_10
Patent number
US08859549B2

Reaction notes

Loading…