Dimethyl Sulfoxide → HCID 58923365, compound

HRID 1951055Notes

Reaction equation

HRID 1951055 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][OH:5].F[C:8]1[CH:9]=[C:10]2[C:19](=[CH:20][CH:21]=1)[C:18](=[O:22])[C:17]1[C:16]([OH:23])=[CH:15][C:14]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[CH:13][C:12]=1N2.CS(C)=[O:32]>CCOC(C)=O.[NH4+].[Cl-]>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][O:5][C:8]1[CH:9]=[C:10]2[C:19](=[CH:20][CH:21]=1)[C:18](=[O:22])[C:17]1[C:16]([OH:23])=[CH:15][C:14]([N:24]3[CH2:29][CH2:28][O:27][CH2:26][CH2:25]3)=[CH:13][C:12]=1[O:32]2

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 79022-(Dimethylamino)ethanolHCID 69450122HCID 69450122, compound

Product 1

HCID 58923365HCID 58923365, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A suspension of KH (about 3 mg, 30-35% by weight in mineral oil) was added to a solution of N,N-dimethylethanolamine (14 mg, 0.16 mmol) and 6-fluoro-1-hydroxy-3-morpholin-4-yl-10H-acridin-9-one (25 mg, 0.08 mmol) in DMSO (1.0 mL), and the reaction mixture was heated at reflux for 4 hours. After cooling, the mixture was diluted with EtOAc and sat. NH4Cl. The organic layer was washed six times with water. The organics were dried (Na2SO4), then concentrated. The concentrate was purified via flash chromatography to yield 4 mg (13%). 1H NMR (CDCl3, 400 MHz) δ: 12.94 (s, 1H), 8.11 (d, 1H), 6.93 (d, 1H), 6.81 (s, 1H), 6.25 (d, 1H), 4.17 (t, 3H), 3.86-3.84 (m, 4H), 3.37-3.35 (m, 4H), 2.80 (t, 2H), 2.39 (s, 6H). LRMS (APCI, positive): Da/e 384.5 (m+1).

Workup

  1. additionA suspension of KH (about 3 mg, 30-35% by weight in mineral oil)
  2. temperaturethe reaction mixture was heated
  3. temperatureat reflux for 4 hours
  4. temperatureAfter cooling
  5. washThe organic layer was washed six times with water
  6. dry with materialThe organics were dried (Na2SO4)
  7. concentrationconcentrated
  8. customThe concentrate was purified via flash chromatography
  9. customto yield 4 mg (13%)

Sources & evidence

ORD record
ord-6caf60c77a934e4bb67bbc35e9f0a740
Source dataset
uspto-grants-2013_03
Patent number
US08404681B2

Reaction notes

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