Ethylenediamine → HCID 178438780, compound

HRID 861018Notes

Reaction equation

HRID 861018 reaction equation
[CH3:1][S:2]([C:5]([C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]4[CH:25]=[C:26]5[N:32]=[CH:31][N:30](COCC[Si](C)(C)C)[C:27]5=[N:28][CH:29]=4)[CH:19]=3)[CH:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2)([CH3:7])[CH3:6])(=[O:4])=[O:3].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C(N)CN>CN(C=O)C.O>[N:32]1[C:26]2[C:27](=[N:28][CH:29]=[C:24]([C:20]3[CH:19]=[C:18]([C:16]4[CH:17]=[C:8]([C:5]([S:2]([CH3:1])(=[O:4])=[O:3])([CH3:6])[CH3:7])[CH:9]=[C:10]5[C:15]=4[N:14]=[CH:13][CH:12]=[CH:11]5)[CH:23]=[CH:22][CH:21]=3)[CH:25]=2)[NH:30][CH:31]=1

Participants

6

Reactant 3

HCID 3301EthylenediamineHCID 2724141Tetrabutylammonium FluorideHCID 69374330HCID 69374330, compound

Product 1

HCID 178438780HCID 178438780, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 6-(1-methanesulfonyl-1-methyl-ethyl)-8-{3-[3-(2-trimethylsilanyl-ethoxymethyl)-3H-imidazo[4,5-b]pyridin-6-yl]-phenyl}-quinoline from Step 2 (1.0 eq.), TBAF (2.0 eq.) and ethylene diamine (1.5 eq.) in DMF (0.2M) was stirred at 80° C. for 3 h. The mixture was cooled, diluted with water, filtered. The resulting solid was stirred in acetone to afford the title compound after filtration. 1H NMR (500 MHz, DMSO-d6): δ 8.94 (dd, 1H), 8.72 (s, 1H), 8.52 (dd, 1H), 8.47 (s, 1H), 8.30–8.25 (m, 2H), 8.08 (d, 1H), 7.98 (s, 1H), 7.79 (d, 1H), 7.68 (d, 1H), 7.63–7.60 (m, 2H), 2.81 (s, 3H), 1.93 (s, 6H).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. stirringThe resulting solid was stirred in acetone

Sources & evidence

ORD record
ord-5b0046315c0e43d0864ad78ea681174e
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

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