Methanol → HCID 50898963, compound

HRID 390104Notes

Reaction equation

HRID 390104 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:16])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:4]([C:17]2[C:25]3[C:20](=[N:21][CH:22]=[CH:23][N:24]=3)[N:19](S(C3C=CC=CC=3)(=O)=O)[CH:18]=2)[CH:3]=1.[OH-].[Na+].CO>O1CCOCC1>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C:9](=[O:16])[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:5]=[C:4]([C:17]2[C:25]3[C:20](=[N:21][CH:22]=[CH:23][N:24]=3)[NH:19][CH:18]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 87181084HCID 87181084, compound

Product 1

HCID 50898963HCID 50898963, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of EXAMPLE 17A (40.0 mg, 0.082 mmol) and 20% sodium hydroxide (0.1 mL) in dioxane (1.5 mL) was heated at 50° C. for 2 h. The mixture was concentrated and the residue treated with water, sonicated, filtered, and washed with water. The solids were dissolved in 6 mL hot 1:1 dimethylsulfoxide/methanol. After cooling, a precipitate formed and additional methanol was added. The solids were filtered, washed with methanol, and dried to give 14.0 mg (32%) of the title compound. 1H NMR (300 MHz, DMSO-D6) 7.41-7.67 (m, 3H), 7.95-8.16 (m, 3H), 8.39 (d, J=2.4 Hz, 1H), 8.60 (d, J=2.8 Hz, 1H), 8.77 (s, 1H), 9.08 (d, J=1.2 Hz, 1H), 10.98 (s, 1H), 12.74 (s, 1H). MS (ESI) m/z 350.5 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue treated with water
  3. customsonicated
  4. filtrationfiltered
  5. washwashed with water
  6. dissolutionThe solids were dissolved in 6 mL hot 1:1 dimethylsulfoxide/methanol
  7. temperatureAfter cooling
  8. customa precipitate formed
  9. filtrationThe solids were filtered
  10. washwashed with methanol
  11. customdried

Sources & evidence

ORD record
ord-2bcdd7cc31c7422aacd25ca972dacf65
Source dataset
uspto-grants-2013_02
Patent number
US08383624B2

Reaction notes

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