Potassium tert-butoxide → HCID 67443434, compound

HRID 1400806Notes

Reaction equation

HRID 1400806 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]3[N:16]=[CH:15][C:14]([CH2:17][N:18]([CH2:26][CH2:27][O:28][CH3:29])[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:13][CH:12]=3)[S:10][C:3]=12.Cl.[NH2:31][C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][N:33]=1.CC(C)([O-])C.[K+]>CS(C)=O>[NH2:31][C:32]1[N:33]=[CH:34][C:35]([O:38][C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[CH:8]=[C:9]([C:11]4[N:16]=[CH:15][C:14]([CH2:17][N:18]([CH2:26][CH2:27][O:28][CH3:29])[C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:13][CH:12]=4)[S:10][C:3]=23)=[CH:36][CH:37]=1

Participants

5

Reactant 3

HCID 23665647Potassium tert-butoxideHCID 457908886-Aminopyridin-3-ol--hydrogen chloride (1/1)HCID 57919613tert-Butyl ((6-(7-chlorothieno[3,2-b]pyridin-2-yl)pyridin-3-yl)methyl)(2-methoxyethyl)carbamate

Product 1

HCID 67443434HCID 67443434, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

A stirred suspension of 22 (1.0 g, 2.3 mmol), 2-amino-5-hydroxypyridine hydrochloride (405 mg, 2.77 mmol) and potassium tert-butoxide (817 mg, 6.91 mmol) in DMSO (20 mL) under nitrogen was heated to 95° C. for 1 hr then cooled to RT. The reaction mixture was then partitioned between water and AcOEt. The organic layer was successively washed with water, 0.1 N NaOH, a saturated aqueous solution of sodium bicarbonate, a saturated aqueous solution of ammonium chloride and brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was purified twice by Biotage (SNAP 50 g cartridge; MeOH/DCM: 0/100 to 10/90 over 20 CV and Silia Flash 80 g; MeOH/DCM: 0/100 to 10/90 over 20 CV), to afford the title compound 27 (634 mg, 1.249 mmol, 54% yield) as pale yellow sticky oil. MS (m/z): 508.6 (M+H).

Workup

  1. temperaturethen cooled to RT
  2. customThe reaction mixture was then partitioned between water and AcOEt
  3. washThe organic layer was successively washed with water, 0.1 N NaOH
  4. dry with materiala saturated aqueous solution of sodium bicarbonate, a saturated aqueous solution of ammonium chloride and brine, dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified twice by Biotage (SNAP 50 g cartridge; MeOH/DCM: 0/100 to 10/90 over 20 CV and Silia Flash 80 g; MeOH/DCM: 0/100 to 10/90 over 20 CV)

Sources & evidence

ORD record
ord-e2455d4e02514203850bbc41039255c4
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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