Sodium Hydroxide → HCID 178521600, compound

HRID 1947004Notes

Reaction equation

HRID 1947004 reaction equation
[OH-].[Na+].C1(S([N:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:14]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([NH:27][C@H:28]4[CH2:33][CH2:32][C@H:31]([OH:34])[CH2:30][CH2:29]4)[N:22]=3)=[CH:13]2)(=O)=O)C=CC=CC=1>CO>[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([C:21]2[CH:26]=[CH:25][N:24]=[C:23]([NH:27][C@H:28]3[CH2:29][CH2:30][C@H:31]([OH:34])[CH2:32][CH2:33]3)[N:22]=2)=[CH:13]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 178527312HCID 178527312, compound

Product 1

HCID 178521600HCID 178521600, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaOH (200 mg, 5 mmol) was added to a solution of trans-4-[4-(1-benzenesulfonyl-1H-indol-3-yl)-pyrimidin-2-ylamino]-cyclohexanol (296 mg, 0.66 mmol) in MeOH (15 mL), and the resulting mixture stirred at RT for 6 h. The reaction mixture was concentrated under reduced pressure, the residue neutralized by addition of aqueous HCl (1 M), and then partitioned between water and EtOAc. The organic layer was separated, washed with water, dried over Na2SO4, filtered and evaporated under reduced pressure to give a crude yellow solid. This crude material was purified by flash chromatography (MeOH/DCM, 5:95) to give trans-4-[4-(1H-indol-3-yl)-pyrimidin-2-ylamino]-cyclohexanol (115 mg, 57% yield) as a white powder. MS=309 [M+H]+; MP=258.1-259.9° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue neutralized by addition of aqueous HCl (1 M)
  3. custompartitioned between water and EtOAc
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customto give a crude yellow solid
  10. customThis crude material was purified by flash chromatography (MeOH/DCM, 5:95)

Sources & evidence

ORD record
ord-6169613518644fdea24aa09cc0772376
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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