N,N-Dimethylethylenediamine → HCID 66717189, compound

HRID 2409562Notes

Reaction equation

HRID 2409562 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[S:15][C:14]3=[N:16][CH:17]=[C:18]([C:19]4[CH:20]=[N:21][C:22](S(C)=O)=[N:23][CH:24]=4)[N:13]3[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[CH3:28][N:29]([CH3:33])[CH2:30][CH2:31][NH2:32]>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[S:15][C:14]3=[N:16][CH:17]=[C:18]([C:19]4[CH:24]=[N:23][C:22]([NH:32][CH2:31][CH2:30][N:29]([CH3:33])[CH3:28])=[N:21][CH:20]=4)[N:13]3[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 66717188HCID 66717188, compound

Product 1

HCID 66717189HCID 66717189, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
85 °C

Procedure

2-(3,4-Dimethoxy-phenyl)-5-(2-methanesulfinyl-pyrimidin-5-yl) -imidazo[2,1-b][1,3,4]thiadiazole (66 mg, 0.164 mmol, 1 eq) was dissolved in 1,4-dioxane (min. volume) at 75° C. N,N-dimethylethylenediamine (0.053 ml, 0.493 mmol, 3 eq) was added, and the solution was heated at 85° C. for 4 h. The solvent was removed, and the residue was triturated in Et2O, filtered and washed with more solvent to give the desired product as a pale yellow solid (46 mg, 66%). HPLC-MS: (5-100% B in 8 min, 0.8 mL/min, 50° C.): tR=2.87 min, [M+H]+ m/z 426.3; 1H NMR (300 MHz, CDCl3) δ 8.84 (s, 2H), 7.43-7.38 (m, 3H), 6.93 (d, J=9.0 Hz, 1H), 5.86 (s, 1H), 3.95 (d, J=9.0 Hz, 7H), 3.52 (dd, J=11.4, 5.7 Hz, 2H), 2.56 (t, J=6.0 Hz, 2H), 2.28 (s, 7H) ppm.

Workup

  1. customThe solvent was removed
  2. customthe residue was triturated in Et2O
  3. filtrationfiltered
  4. washwashed with more solvent

Sources & evidence

ORD record
ord-8295abf739944611b990959229048b3d
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

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