Potassium Carbonate → HCID 86664207, compound

HRID 2409537Notes

Reaction equation

HRID 2409537 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[N:15]3[C:11]([S:12][C:13]([C:16]4[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([O:23][CH3:24])[CH:17]=4)=[N:14]3)=[N:10][C:9]=2[CH3:25])=[CH:4][C:3]=1[C:26]([F:29])([F:28])[F:27].Br[CH2:31][CH2:32][NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[N:15]3[C:11]([S:12][C:13]([C:16]4[CH:21]=[CH:20][C:19]([O:22][CH2:31][CH2:32][NH:33][C:34](=[O:40])[O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[C:18]([O:23][CH3:24])[CH:17]=4)=[N:14]3)=[N:10][C:9]=2[CH3:25])=[CH:4][C:3]=1[C:26]([F:28])([F:27])[F:29]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 136378808HCID 136378808, compound

Product 1

HCID 86664207HCID 86664207, compoundYield 15.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
105 °C

Procedure

To a solution of 4-(5-(6-amino-5-(trifluoromethyl)pyridin-3-yl) -6-methylimidazo[2,1-b][1,3,4]thiadiazol-2-yl)-2-methoxyphenol (0.030 g, 0.07 mmol, 1 eq) in dry DMF (0.8 mL), tert-butyl 2-bromoethylcarbamate (0.020 g, 0.09 mmol, 1.25 eq) and K2CO3 (0.01 g, 0.09 mmol, 1.25 eq) were added. The mixture was stirred at 105° C. for 2 h and cooled to RT. The solvent was evaporated, and the dry residue was taken up in DCM, washed with water (2×1 mL), dried (MgSO4), filtered and concentrated to dryness. Purification by preparative HPLC (RP-C18, ACN/water) gave the desired product (0.006 g, 15%). HPLC-MS: (50-100% B in 8 min, 0.8 mL/min): tR=1.75 min, [M+H]+ m/z 565; 1H NMR (300 MHz, CDCl3) δ/ppm 8.42 (d, J=1.7, 1H), 7.95 (d, J=1.8, 1H), 7.49 (s, 1H), 7.41 (t, J=2.5, 1H), 7.32 (t, J=4.5, 1H), 5.19 (s, 2H), 5.01 (s, 1H), 3.99 (s, 3H), 3.48-3.43 (m, 2H), 2.40-2.32 (m, 3H), 2.19-2.07 (m, 8H), 1.98 (s, 3H).

Workup

  1. temperaturecooled to RT
  2. customThe solvent was evaporated
  3. washwashed with water (2×1 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customPurification by preparative HPLC (RP-C18, ACN/water)

Sources & evidence

ORD record
ord-24030dfd6df84116baecde4eb6d5ba62
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

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