Ammonia → 2-[8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-thieno[3,2-b]pyridine-3-carbonitrile

HRID 226079Notes

Reaction equation

HRID 226079 reaction equation
Br[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[S:4][C:3]=1[C:11]1[N:15]2[N:16]=[C:17]([CH3:25])[CH:18]=[C:19]([CH:20]([CH2:23][CH3:24])[CH2:21][CH3:22])[C:14]2=[N:13][C:12]=1[CH3:26].[Cu][C:28]#[N:29].CN(C=O)C.N>CO.CCOC(C)=O.CCCCCC>[CH2:21]([CH:20]([C:19]1[C:14]2[N:15]([C:11]([C:3]3[S:4][C:5]4[C:6](=[N:7][CH:8]=[CH:9][CH:10]=4)[C:2]=3[C:28]#[N:29])=[C:12]([CH3:26])[N:13]=2)[N:16]=[C:17]([CH3:25])[CH:18]=1)[CH2:23][CH3:24])[CH3:22]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 6228DimethylformamideHCID 577526393-(3-Bromo-thieno[3,2-b]pyridin-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazineHCID 178418546HCID 178418546, compound

Product 1

HCID 688563762-[8-(1-Ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-thieno[3,2-b]pyridine-3-carbonitrileYield 16%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8058HexaneSolvent2×HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
120 °C

Procedure

50 mg of 3-(3-Bromo-thieno[3,2-b]pyridin-2-yl)-8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazine (0.12 mmol) and 32 mg of copper (I) cyanide (0.36 mmol) are placed into a reaction vial with 2.0 ml of dry DMF. The vial is capped with a Teflon cap and heated at 120° C. overnight. The reaction mixture is applied onto a silica-gel chromatography column (1st column; Hexane:AcOEt=5:1, 2nd column; Hexane:AcOEt:2M NH3 in MeOH=20:4:1) to give 7.2 mg of the title compound (16%). mass spectrum (m/e): 376; 1H-NMR (CDCl3): 8.86 (m, 1H), 8.22 (m, 1H), 7.40 (dd, 1H, J=8.2 Hz, 4.6 Hz), 6.83 (s, 1H), 3.32 (m, 1H), 2.73 (s, 3H), 2.60 (s, 3H), 1.85 (m, 4H), 0.88 (t, 6H, J=7.5 Hz) ppm.

Workup

  1. customcap

Sources & evidence

ORD record
ord-9555222559e84e6a8607b46fd7ecd73c
Source dataset
uspto-grants-2009_07
Patent number
US07557103B2

Reaction notes

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