Water → HCID 44160140, compound

HRID 1926337Notes

Reaction equation

HRID 1926337 reaction equation
C(OC([N:6]1[CH:11]2[CH2:12][CH2:13][CH:7]1[CH2:8][CH:9]([N:14]1[CH:18]=[C:17]([C:19]3[CH:20]=[N:21][C:22]([NH:34]C(OCC)=O)=[C:23]([C:25]4[S:26][C:27]5[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=5[N:29]=4)[CH:24]=3)[CH:16]=[N:15]1)[CH2:10]2)=O)C.[OH-].[K+].O.NN.O>C(O)CO>[CH:11]12[NH:6][CH:7]([CH2:13][CH2:12]1)[CH2:8][CH:9]([N:14]1[CH:18]=[C:17]([C:19]3[CH:24]=[C:23]([C:25]4[S:26][C:27]5[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=5[N:29]=4)[C:22]([NH2:34])=[N:21][CH:20]=3)[CH:16]=[N:15]1)[CH2:10]2

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 67521042HCID 67521042, compound

Product 1

HCID 44160140HCID 44160140, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
200 °C

Procedure

To a stirring solution of 3-[4-(5-benzothiazol-2-yl-6-ethoxycarbonylaminopyridin-3-yl)-pyrazol-1-yl]-8-azabicyclo[3.2.1]octane-8-carboxylic acid ethyl ester (7.1 mg, 0.013 mmol, 1 eq) and potassium hydroxide (22.2 mg, 0.396 mmol, 30 eq) in 1,2-ethanediol (3 mL), hydrazine hydrate (7 μL, 0.1 mmol, 10 eq) was added and the solution was stirred at reflux (T=200° C.) for 9 h. The reaction mixture was poured into water and extracted with ether. The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was purified by prep. TLC [Silicycle, 1000 μm, 20×20 cm plate, developed twice in a 8% 7N NH3(MeOH):CH2Cl2 solvent system.] The desired band was scraped from the plate, the silica gel was completely rinsed of all product, and the filtrate was concentrated in vacuo, giving the title compound as a yellow solid. MS (ES+): m/z=403.17 (40) [MH+]. HPLC: tR=2.37 min (ZQ3, polar—5 min).

Workup

  1. extractionextracted with ether
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by prep
  6. washthe silica gel was completely rinsed of all product
  7. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-ab5d5ad69c384d4daf45db96a0a8440f
Source dataset
uspto-grants-2012_05
Patent number
US08178668B2

Reaction notes

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