Hydrochloric Acid → 6-((4-(4-cyano-5-(dicyanomethylene)-1-hexyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)phenyl)(2-ethylhexyl)amino)hexanoic acid
Reaction equation
[C:1]1([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([O:15]C)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:17](=[O:20])([O-])[O-].[K+].[K+].Br[CH2:24][CH:25]([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:26][CH3:27].C(OCCCCCCN(CC(CC)CCCC)C1C=CC=CC=1)(=O)C.C(OC(=O)C)(=O)C.[Na].[Na].C(C1C(=C(C#N)C#N)NC(=O)C=1O)#N.O=P(Cl)(Cl)Cl.BrCCCCCC.[C:92]([C:94]1[C:98](=[C:99]([C:102]#[N:103])[C:100]#[N:101])[N:97]([CH2:104][CH2:105][CH2:106][CH2:107][CH2:108][CH3:109])C(=O)[C:95]=1C1C=CC(N(CC(CC)CCCC)CCCCCC(OC)=O)=CC=1)#[N:93].Cl>O1CCCC1.CN(C)C=O>[C:92]([C:94]1[C:98](=[C:99]([C:100]#[N:101])[C:102]#[N:103])[N:97]([CH2:104][CH2:105][CH2:106][CH2:107][CH2:108][CH3:109])[C:17](=[O:20])[C:95]=1[C:4]1[CH:3]=[CH:2][C:1]([N:7]([CH2:24][CH:25]([CH2:26][CH3:27])[CH2:28][CH2:29][CH2:30][CH3:31])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]([OH:15])=[O:14])=[CH:6][CH:5]=1)#[N:93]Participants
Reactant 10
HCID 313Hydrochloric Acid
HCID 7918Acetic Anhydride
HCID 81011-Bromohexane
HCID 11430Potassium Carbonate2×
HCID 24813Phosphorus oxychloride
HCID 868042-Ethylhexyl bromide
HCID 20441676Methyl 6-(phenylamino)hexanoate
HCID 578577296-((2-Ethylhexyl)(phenyl)amino)hexyl acetate
HCID 866340934-Cyano-5-dicyanomethylene-3-hydroxy-2-oxo-3-pyrroline disodium salt
HCID 86634096methyl 6-((4-(4-cyano-5-(dicyanomethylene)-1-hexyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)phenyl)(2-ethylhexyl)amino)hexanoateProduct 1
Reagents, catalysts & solvents 2
Procedure
A precursor 9 (methyl 6-((2-ethylhexyl)(phenyl)amino)hexanoate) is obtained by reacting methyl 6-(phenylamino)hexanoate, potassium carbonate, dimethylformamide, and 3-(bromomethyl)heptane. Then, 6-((2-ethylhexyl)(phenyl)amino)hexyl acetate, dimethylformamide, acetic anhydride, 4-cyano-5-dicyanomethylene-3-hydroxy-2-oxo-3-pyrroline disodium salt, and POCl3 are reacted to thus prepare a precursor 10 (methyl6-((4-(4-cyano-5-(dicyanomethyene)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)phenyl)(2-ethylhexyl)amino) hexanoate). Then, methyl 6-((4-(4-cyano-5-(dicyanomethylene)-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)phenyl)(2-ethylhexyl)amino) hexanoate, potassium carbonate, dimethylformamide, and 1-bromohexane are reacted to thus produce methyl 6-((4-(4-cyano-5-(dicyanomethyene)-1-hexyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)phenyl)(2-ethylhexyl)amino)hexanoate, which is then reacted with tetrahydrofuran and hydrochloric acid, yielding a precursor 11 (6-((4-(4-cyano-5-(dicyanomethylene)-1-hexyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)phenyl)(2-ethylhexyl)amino) hexanoic acid). Then, 6-((2-ethylhexyl)(phenyl)amino)hexyl acetate, 6-((4(4-cyano-5-(dicyanomethylene)-1-hexyl-2-oxo-2,5-dihydro-1H-pyrrol)-3-yl)phenyl)(2-ethylhexyl)amino)hexanoic acid, DPTS, dicyclohexyl carbodiimide, and dichloromethyl are reacted together, thus obtaining a precursor 12 ((9-(6-(tert-butyldimethylsilyloxy)hexyl)-9H-carbazol-3-yl)methyl 6-((4-(4-cyano-5-(dicyanomethylene)-1-hexyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)phenyl)(2-ethylhexyl)amino)hexanoate). Then, (9-(6-(tert-butyldimethylsilyloxy)hexyl)-9H-carbazol-3-yl)methyl 6-((4-(4-cyano-5-(dicyanomethylene)-1-hexyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)phenyl)(2-ethylhexyl)amino)hexanoate, tetrahydrofuran, and hydrochloric acid are reacted together, yielding a compound 13 ((9-(6-hydrohexyl)-9H-carbazol-3-yl)methyl6-((4-(4-cyano-5-(dicyanomethylene)-1-hexyl-2-oxo-2,5-dihydro-1H-pyrrol-3-yl)phenyl)(2-ethylhexyl)amino)hexanoate). The compound 13 is the dendron compound represented by Formula 6 according to exemplary embodiments.
Sources & evidence
- ORD record
- ord-28cb6cff87094f9e8bc1e95f1a902567
- Source dataset
- uspto-grants-2011_03
- Patent number
- US07915428B2
Reaction notes
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