Sodium Hydroxide → HCID 57725598, compound

HRID 2370574Notes

Reaction equation

HRID 2370574 reaction equation
[CH:1]1([CH2:7][NH:8][C:9]2[S:10][C:11]3[CH:17]=[C:16]([O:18][C:19]4[CH:24]=[CH:23][N:22]=[C:21]([C:25](OC(C)(C)C)=[O:26])[CH:20]=4)[CH:15]=[CH:14][C:12]=3[N:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[Al]>C1COCC1.O.CO>[CH:1]1([CH2:7][NH:8][C:9]2[S:10][C:11]3[CH:17]=[C:16]([O:18][C:19]4[CH:24]=[CH:23][N:22]=[C:21]([CH2:25][OH:26])[CH:20]=4)[CH:15]=[CH:14][C:12]=3[N:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 5359268AluminumHCID 21226445Aluminium lithium hydrideHCID 57725685HCID 57725685, compound

Product 1

HCID 57725598HCID 57725598, compoundYield 37.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To the solution of tert-butyl 4-(2-(cyclohexylmethylamino)benzo[d]thiazol-6-yloxy)picolinate (420 mg, 1.14 mmol) under argon in 50 ml of THF was added 1 M LAH solution in THF (3.41 ml, 3.41 mmol) slowly at room temperature. The reaction mixture was stirred at room temperature for 30 minutes. The crude reaction mixture was worked up by carefully adding methanol (5 ml), then 6M NaOH (5 ml), and water (5 ml) with stirring at room temperature. The aluminum salts were allowed to precipitate out. Ethyl acetate (200 ml) was added and the organic layer was decanted off from salts. The salts were washed again with ethyl acetate (100 ml) and decanted. The organic layers were combined and washed with brine (2×50 ml), dried with Na2SO4, filtered and concentrated. The resulting solid residue was purified by silica gel column chromatography, eluted with (5% methanol 95% DCM) and concentrated in vaccuo to give (4-(2-(cyclohexylmethylamino)benzo[d]thiazol-6-yloxy)pyridin-2-yl)methanol as solid (157 mg). ES/MS m/z 370.2 (MH+).

Workup

  1. customThe crude reaction mixture
  2. customto precipitate out
  3. additionEthyl acetate (200 ml) was added
  4. customthe organic layer was decanted off from salts
  5. washThe salts were washed again with ethyl acetate (100 ml)
  6. customdecanted
  7. washwashed with brine (2×50 ml)
  8. dry with materialdried with Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe resulting solid residue was purified by silica gel column chromatography
  12. washeluted with (5% methanol 95% DCM)
  13. concentrationconcentrated in vaccuo

Sources & evidence

ORD record
ord-5abc8199582847fd81a2eb0701e76890
Source dataset
uspto-grants-2014_04
Patent number
US08710048B2

Reaction notes

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