Dimethylamine → HCID 57933009, compound

HRID 1432724Notes

Reaction equation

HRID 1432724 reaction equation
Br[C:2]1[O:3][C:4]([Br:23])=[C:5]([C:7]2[N:11]3[N:12]=[C:13]([CH3:21])[CH:14]=[C:15]([CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[C:10]3=[N:9][C:8]=2[CH3:22])[N:6]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:30][NH:31][CH3:32].C1COCC1>>[Br:23][C:4]1[O:3][C:2]([N:31]([CH3:32])[CH3:30])=[N:6][C:5]=1[C:7]1[N:11]2[N:12]=[C:13]([CH3:21])[CH:14]=[C:15]([CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[C:10]2=[N:9][C:8]=1[CH3:22]

Participants

5

Reactant 4

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 68844259HCID 68844259, compound

Product 1

HCID 57933009HCID 57933009, compoundYield 87%

Conditions

Temperature
130 °C

Procedure

67 mg of 3-(2,5-Dibromo-oxazol-4-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.15 mmol), 146 mg of cesium carbonate (0.45 mmol) and 3.0 ml of dimethylamine 2.0M in THF (6 mmol) are placed into a 4 ml of reaction vial and the vial is capped with a Teflon cap. The reaction vial is heated at 130° C. overnight. The reaction mixture is concentrated and applied onto a silica-gel chromatography column (Hexane:AcOE t=3:1) to give 53 mg of the title compound (87%); mass spectrum (m/e): 406; 1H-NMR (CDCl3): 6.72 (s, 1H), 3.37 (m, 1H), 3.15 (s, 6H), 2.58 (s, 3H), 2.53 (s, 3H), 1.85 (m, 4H), 0.90 (t, 6H, J=7.2 Hz).

Workup

  1. customcap
  2. customThe reaction
  3. concentrationThe reaction mixture is concentrated

Sources & evidence

ORD record
ord-720aa2b924aa4709afbf1e3d8a7349be
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

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