Water → HCID 118092988, compound

HRID 708912Notes

Reaction equation

HRID 708912 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH2:13][C:14]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=1[CH:23]([C:29]#[N:30])C(OCC)=O)[CH3:12])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl-].[Li+].O>CS(C)=O.CCOC(C)=O>[C:29]([CH2:23][C:15]1[CH:16]=[CH:17][C:18]([N+:20]([O-:22])=[O:21])=[CH:19][C:14]=1[CH2:13][N:11]([CH3:12])[C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)#[N:30]

Participants

6

Reactant 3

HCID 962WaterHCID 433294Lithium ChlorideHCID 118101219HCID 118101219, compound

Product 1

HCID 118092988HCID 118092988, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

36B (2.609 g, 6.34 mmol) was dissolved in DMSO (40 mL), lithium chloride (0.538 g, 12.68 mmol) and water (0.114 mL, 6.34 mmol) were added. The reaction mixture was stirred at 130° C. for 2 h, then cooled to rt, diluted with EtOAc (250 mL), washed with water (2×100 mL), brine (1×100 mL) and dried (Na2SO4). EtOAc was removed under reduced pressure and the residue was purified by flash chromatography (0-70% EtOAc/hexanes) to give 36C (1.803 g, 5.31 mmol, 84% yield) as a yellowish film. MS (ESI) m/z: 340.1 [M+1]+. 1H NMR: (400 MHz, CDCl3) δ ppm 8.20 (1H, d, J=7.07 Hz), 8.09 (1H, br. s.), 7.67 (1H, d, J=5.05 Hz), 7.29-7.46 (5H, m), 5.19 (2H, s), 4.59 (2H, br. s.), 3.91 (2H, br. s.), 2.94 (3H, br. s.).

Workup

  1. temperaturecooled to rt
  2. washwashed with water (2×100 mL), brine (1×100 mL)
  3. dry with materialdried (Na2SO4)
  4. customEtOAc was removed under reduced pressure
  5. customthe residue was purified by flash chromatography (0-70% EtOAc/hexanes)

Sources & evidence

ORD record
ord-0001a67c670b40a996b9ef8bf1be08b3
Source dataset
uspto-grants-2015_11
Patent number
US09174974B2

Reaction notes

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