Ethylenediamine → HCID 135820472, compound

HRID 1988968Notes

Reaction equation

HRID 1988968 reaction equation
[CH3:1][N:2]([CH3:41])[CH2:3][CH2:4][CH2:5][NH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12](COCC[Si](C)(C)C)[N:11]=[C:10]2[C:24]1[N:28](COCC[Si](C)(C)C)[C:27]2[CH:37]=[CH:38][CH:39]=[CH:40][C:26]=2[N:25]=1.C(N)CN.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[NH:28]1[C:27]2[CH:37]=[CH:38][CH:39]=[CH:40][C:26]=2[N:25]=[C:24]1[C:10]1[C:9]2[C:13](=[CH:14][CH:15]=[C:7]([NH:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:1])[CH3:41])[CH:8]=2)[NH:12][N:11]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 2724141Tetrabutylammonium FluorideHCID 22056020HCID 22056020, compound

Product 1

HCID 135820472HCID 135820472, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A solution of N,N-dimethyl-N′-{1-(2-trimethylsilanyl-ethoxymethyl)-3-[1-(2-trimethylsilanyl-ethoxymethyl)-1H-benzimidazol-2-yl]-1H-indazol-5-yl}-propane-1,3-diamine in THF was treated with ethylene diamine (20 equivalents) and tetrabutylammonium fluoride (20 equivalents) and heated at 70° C. overnight. The resulting crude residue was purified by reverse phase HPLC to N′-[3-(1H-Benzoimidazol-2-yl)-1H-indazol-5-yl]-N,N-dimethyl-propane-1,3-diamine. LC/MS (m/z) 335.1 (MH+), Rt 1.30 minutes.

Workup

  1. customThe resulting crude residue was purified by reverse phase HPLC to N′-[3-(1H-Benzoimidazol-2-yl)-1H-indazol-5-yl]-N,N-dimethyl-propane-1,3-diamine

Sources & evidence

ORD record
ord-b55103a38a964f088023594061a62219
Source dataset
uspto-grants-2010_01
Patent number
US07642278B2

Reaction notes

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