Hydrochloric Acid → HCID 90412294, compound

HRID 1522039Notes

Reaction equation

HRID 1522039 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:29][CH3:30])=[C:6]([C:8]2[C:13]([C:14]#[N:15])=[CH:12][N:11]=[C:10]3[N:16](S(C4C=CC=CC=4)(=O)=O)[C:17](I)=[CH:18][C:9]=23)[CH:7]=1.[C:31](=[O:34])([O-])[O-:32].[Na+].[Na+].[OH-].[Li+].Cl.O1[CH2:44][CH2:43][CH2:42][CH2:41]1>O>[C:14]([C:13]1[C:8]([C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[O:29][CH3:30])=[C:9]2[CH:18]=[C:17]([C:42]3[CH2:43][CH:44]4[N:11]([C:31]([O:32][C:6]([CH3:8])([CH3:7])[CH3:5])=[O:34])[CH:10]([CH:41]=3)[CH2:9][CH2:18]4)[NH:16][C:10]2=[N:11][CH:12]=1)#[N:15]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 90412168HCID 90412168, compound

Product 1

HCID 90412294HCID 90412294, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of Example 236C (0.4 g, 0.750 mmol), Example 223B (0.302 g, 0.900 mmol), sodium carbonate (0.238 g, 2.250 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]dichloro-palladium(II) dichloromethane adduct (0.043 g, 0.053 mmol) in 10 mL tetrahydrofuran and 3 mL water was heated at 80° C. for 4 hours. The mixture was cooled to room temperature and treated with 2N lithium hydroxide (1.875 mL, 3.75 mmol) for 4 hours. The mixture was neutralized with 2N aqueous hydrochloric acid and extracted with ethyl acetate. The organic phase was washed with water and brine, dried over sodium sulfate, filtered and concentrated. The residue was purified by flash chromatography eluting with 0-5% methanol in dichloromethane to afford the title compound. MS (ESI(+)) m/e 475 (M+H)+.

Workup

  1. customwas heated at 80° C. for 4 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography
  8. washeluting with 0-5% methanol in dichloromethane

Sources & evidence

ORD record
ord-d0ced0e4215244bda09642538964329e
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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