Potassium Carbonate → HCID 66717245, compound

HRID 2409539Notes

Reaction equation

HRID 2409539 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.Cl[CH2:32][CH2:33][N:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1.C(N(C(C)C)C(C)C)C.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[O:37]1[CH2:38][CH2:39][N:34]([CH2:33][CH2:32][O:22][C:19]2[CH:20]=[CH:21][C:16]([C:13]3[S:12][C:11]4=[N:10][C:9]([CH3:25])=[C:8]([C:5]5[CH:4]=[C:3]([C:26]([F:28])([F:27])[F:29])[C:2]([NH2:1])=[N:7][CH:6]=5)[N:15]4[N:14]=3)=[CH:17][C:18]=2[O:23][CH3:24])[CH2:35][CH2:36]1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 136378808HCID 136378808, compound

Product 1

HCID 66717245HCID 66717245, 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), 4-(2-chloroethyl)morpholine hydrochloride (0.024 g, 0.13 mmol, 1.25 eq), iPr2EtN (0.021 mL, 0.13 mmol, 1.3 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 reversed-phase chromatography (RP-C18, ACN/water) using a pre-packed cartridge and, subsequently, preparative HPLC gave the desired product. HPLC-MS: (5-100% B in 8 min, 0.6 mL/min): tR=3.3 min, [M+H]+ m/z 534.1; 1H NMR (300 MHz, CDCl3) δ/ppm 8.44 (d, J=1.7, 1H), 7.98 (d, J=1.8, 1H), 7.49 (d, J=0.8, 1H), 7.41 (d, J=2.0, 1H), 7.31 (d, J=2.1, 1H), 5.07 (s, 2H), 4.01-3.89 (m, 6H), 3.69-3.59 (m, 4H), 3.47 (s, 3H), 2.62-2.51 (m, 3H), 2.38 (dd, J=9.0, 2.7, 7H).

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 reversed-phase chromatography (RP-C18, ACN/water)

Sources & evidence

ORD record
ord-5a7c541d347c4084be13469c635c050c
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

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