Potassium Carbonate → HCID 46941040, compound

HRID 2409538Notes

Reaction equation

HRID 2409538 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].Cl[CH2:31][C:32]([N:34]([CH3:36])[CH3:35])=[O:33].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][C:32]([N:34]([CH3:36])[CH3:35])=[O:33])=[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 758862-chloro-N,N-dimethylacetamideHCID 136378808HCID 136378808, compound

Product 1

HCID 46941040HCID 46941040, compound

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 (0.042 g, 0.1 mmol, 1 eq) in dry DMF (1 mL), 2-chloro-N,N-dimethylacetamide (0.016 g, 0.13 mmol, 1.25 eq) and K2CO3 (0.018 g, 0.13 mmol, 1.25 eq) were added. The mixture was stirred at 105° C. for 1 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) and trituration with Et2O gave the desired product. HPLC-MS: (5-100% B in 8 min, 0.8 mL/min): tR=4.68 min, [M+H]+ m/z 507.1; 1H NMR (300 MHz, CDCl3) δ 8.41 (d, J=1.7, 1H), 7.95 (d, J=1.8, 1H), 7.49 (s, 1H), 7.42 (d, J=2.1, 1H), 7.29 (d, J=2.1, 1H), 5.12-5.01 (m, 2H), 4.57 (d, J=9.2, 2H), 4.03-3.90 (m, 3H), 3.47 (s, 2H), 2.92 (s, 3H), 2.82 (s, 3H), 2.37 (d, J=0.6, 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) and trituration with Et2O

Sources & evidence

ORD record
ord-0ace1278a04f4d4cbdd1692af83bc1e1
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

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