Sodium Hydroxide → HCID 90408458, compound

HRID 871103Notes

Reaction equation

HRID 871103 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][N:8]2[C:12]3[CH:13]=[C:14]([C:17]4[CH:22]=[CH:21][N:20]=[C:19]5[N:23](S(C6C=CC(C)=CC=6)(=O)=O)[C:24]([C:26]6[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH:27]=6)=[CH:25][C:18]=45)[CH:15]=[CH:16][C:11]=3[N:10]=[N:9]2)[CH2:3][CH2:2]1.[OH-].[Na+]>O1CCOCC1>[O:1]1[CH2:2][CH2:3][CH:4]([CH2:7][N:8]2[C:12]3[CH:13]=[C:14]([C:17]4[CH:22]=[CH:21][N:20]=[C:19]5[NH:23][C:24]([C:26]6[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH:27]=6)=[CH:25][C:18]=45)[CH:15]=[CH:16][C:11]=3[N:10]=[N:9]2)[CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 90409594tert-butyl 4-(4-(1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-benzo[d][1,2,3]triazol-6-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 90408458HCID 90408458, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of Example 36E (0.530 g, 0.792 mmol) and 5M aqueous sodium hydroxide (0.555 mL, 2.77 mmol) in dioxane (8 mL) was heated at 90° C. for 8 hours. The solvent was evaporated and the residue was treated with ethyl acetate and washed with aqueous NaHCO3. The organic layer was dried over MgSO4, filtered and concentrated until most of solvent was evaporated. The resulting precipitate was filtered, washed with ethyl acetate/ether, and vacuum oven-dried to give the title compound. The filtrate was concentrated and purified on a 4 g column using the ISCO Companion flash system eluting with ethyl acetate to give additional title compound.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was treated with ethyl acetate
  3. washwashed with aqueous NaHCO3
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated until most of solvent
  7. customwas evaporated
  8. filtrationThe resulting precipitate was filtered
  9. washwashed with ethyl acetate/ether, and vacuum
  10. customoven-dried

Sources & evidence

ORD record
ord-b622bf51268944fc803d88513c92e216
Source dataset
uspto-grants-2015_03
Patent number
US08969375B2

Reaction notes

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