Hydrochloric Acid → HCID 66994486, compound

HRID 449265Notes

Reaction equation

HRID 449265 reaction equation
[Cl:1][C:2]1[C:28]([F:29])=[CH:27][CH:26]=[C:25]([F:30])[C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([O:20]C)=[O:19])=[C:16]([F:24])[CH:15]=3)=[CH:12][CH:13]=[C:8]2[N:7]=[N:6]1.[OH-].[Na+].Cl>CO.C1COCC1.O>[Cl:1][C:2]1[C:28]([F:29])=[CH:27][CH:26]=[C:25]([F:30])[C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([C:14]3[CH:23]=[CH:22][C:17]([C:18]([OH:20])=[O:19])=[C:16]([F:24])[CH:15]=3)=[CH:12][CH:13]=[C:8]2[N:7]=[N:6]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66994916HCID 66994916, compound

Product 1

HCID 66994486HCID 66994486, compoundYield 41%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 17 (0.300 g, 0.725 mmol) in methanol (1 ml), THF (2 ml), sodium hydroxide (0.150 g, 3.75 mmol) in water (1 ml) was added and stirred at RT. After 12 h, the pH was adjusted to 7-7.5 using 0.5N HCl and the solid precipitated was filtered, washed with ethyl acetate and petroleum ether and dried under vacuum to afford the title compound as a pale brown solid (0.120 g, 41%). M.P.: 211-213° C. 1H-NMR (δ ppm, DMSO-d6, 400 MHz): 8.65 (d, J=8.8 Hz, 1H), 8.18 (d, J=8.8 Hz, 1H), 8.02 (m, 2H), 7.83 (t, J=7.4 Hz, 1H), 7.60 (dt, J=9.1, 4.8 Hz, 1H), 7.46 (dt, J=9.0, 4.0 Hz, 1H), 6.11 (s, 2H). MS (m/z): 418.70 (M+).

Workup

  1. customthe solid precipitated
  2. filtrationwas filtered
  3. washwashed with ethyl acetate and petroleum ether
  4. customdried under vacuum

Sources & evidence

ORD record
ord-fc03b37591b64a579711b01eee36285a
Source dataset
uspto-grants-2013_07
Patent number
US08481739B2

Reaction notes

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