Hydrochloric Acid → HCID 67003455, compound

HRID 2362662Notes

Reaction equation

HRID 2362662 reaction equation
[Cl:1][C:2]1[C:3]([C:27]2[S:31][C:30]([C:32]3([O:36][CH2:37][O:38][CH3:39])[CH2:35][CH2:34][CH2:33]3)=[N:29][CH:28]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:5]2=[N:6][CH:7]=1.[OH-].[Na+].Cl>CO>[Cl:1][C:2]1[C:3]([C:27]2[S:31][C:30]([C:32]3([O:36][CH2:37][O:38][CH3:39])[CH2:35][CH2:34][CH2:33]3)=[N:29][CH:28]=2)=[C:4]2[CH:10]=[C:9]([C:11]3[CH:12]=[N:13][N:14]([CH3:16])[CH:15]=3)[NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67003422HCID 67003422, compound

Product 1

HCID 67003455HCID 67003455, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of Example 47A (0.074 g, 0.127 mmol) in methanol (1.5 mL) and 2 M aqueous sodium hydroxide solution (0.317 mL, 0.633 mmol) was heated at 75° C. for 15 minutes. The reaction was cooled to ambient temperature, and the pH adjusted to ˜7 with 10% aqueous HCl solution. The resulting suspension was extracted with ethyl acetate. The aqueous layer was extracted with additional ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The concentrate was purified by flash chromatography on a silica gel column with a gradient of 0% to 3% methanol in dichloromethane to provide the title compound. ESI(+) m/z 429.9 [M+H]+.

Workup

  1. extractionThe resulting suspension was extracted with ethyl acetate
  2. extractionThe aqueous layer was extracted with additional ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe concentrate was purified by flash chromatography on a silica gel column with a gradient of 0% to 3% methanol in dichloromethane

Sources & evidence

ORD record
ord-d00a38b567ea48e289367e837fc8a3b2
Source dataset
uspto-grants-2014_04
Patent number
US08691810B2

Reaction notes

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