Potassium Carbonate → HCID 59291610, compound

HRID 1809616Notes

Reaction equation

HRID 1809616 reaction equation
C([O:4][CH2:5][CH2:6][S:7][C:8]1[CH:9]=[N:10][C:11]([NH:22][C:23]2[S:27][N:26]=[C:25]([C:28]3([CH3:37])[CH2:33][CH2:32][N:31]([C:34](=[O:36])[CH3:35])[CH2:30][CH2:29]3)[N:24]=2)=[C:12]([O:14][C:15]2[C:16]([CH3:21])=[N:17][CH:18]=[CH:19][CH:20]=2)[CH:13]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[OH:4][CH2:5][CH2:6][S:7][C:8]1[CH:13]=[C:12]([O:14][C:15]2[C:16]([CH3:21])=[N:17][CH:18]=[CH:19][CH:20]=2)[C:11]([NH:22][C:23]2[S:27][N:26]=[C:25]([C:28]3([CH3:37])[CH2:29][CH2:30][N:31]([C:34](=[O:36])[CH3:35])[CH2:32][CH2:33]3)[N:24]=2)=[N:10][CH:9]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 68707270HCID 68707270, compound

Product 1

HCID 59291610HCID 59291610, compoundYield 44.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(6-(3-(1-acetyl-4-methylpiperidin-4-yl)-1,2,4-thiadiazol-5-ylamino)-5-(2-methylpyridin-3-yloxy)pyridin-3-ylthio)ethyl acetate (89 mg, 0.164 mmol) and potassium carbonate (113 mg, 0.820 mmol) in ethanol (25 mL) was heated at reflux for 2 hr. The reaction was filtered and concentrated, and the residue was purified by reverse phase with 0.1% TFA buffer. The purified fractions were poured into saturated sodium bicarbonate and extracted with methylene chloride to afford 1-(4-(5-(5-(2-hydroxyethylthio)-3-(2-methylpyridin-3-yloxy)pyridin-2-ylamino)-1,2,4-thiadiazol-3-yl)-4-methylpiperidin-1-yl)ethanone (36.8 mg, 0.0735 mmol, 44.8% yield). 1H NMR (d6-DMSO) δ 12.18 (s, 1H), 8.28 (d, 1H), 8.26 (dd, 1H), 7.44 (d, 1H), 7.25-7.15 (m, 2H), (4.89 (m, 1H), 3.89 (m, 1H), 3.60 (m, 1H), 3.52 (m, 2H), 3.18 (t, 1H), 3.00-2.88 (m, 3H), 2.53 (m, 3H), 2.31 (m, 2H), 1.97 (s, 3H), 1.62-1.40 (m, 2H), 1.26 (s, 3H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 hr
  3. filtrationThe reaction was filtered
  4. concentrationconcentrated
  5. customthe residue was purified by reverse phase with 0.1% TFA buffer
  6. additionThe purified fractions were poured into saturated sodium bicarbonate
  7. extractionextracted with methylene chloride

Sources & evidence

ORD record
ord-b3b140bb08f84ecca93445f1f5a09bd2
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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