Borane → N-(3-Dimethylaminopropyl)-N-(3-(1H-imidazol-1-yl)propyl)benz(cd)indol-2-amine

HRID 1090254Notes

Reaction equation

HRID 1090254 reaction equation
N1(CCC(O)=O)C=CN=C1.[CH3:11][N:12]([CH3:26])[CH2:13][CH2:14][CH2:15][NH:16][C:17](=O)[CH2:18][CH2:19][N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1.B.[N:28]1[C:36]2[C:31]3[C:32](=[CH:37][CH:38]=[CH:39][C:30]=3[C:29]=1S)[CH:33]=[CH:34][CH:35]=2>O1CCCC1.C(O)C>[CH3:11][N:12]([CH3:26])[CH2:13][CH2:14][CH2:15][N:16]([CH2:17][CH2:18][CH2:19][N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1)[C:29]1[C:30]2[CH:39]=[CH:38][CH:37]=[C:32]3[C:31]=2[C:36](=[CH:35][CH:34]=[CH:33]3)[N:28]=1

Participants

7

Reactant 4

HCID 6331BoraneHCID 27947183-(1H-imidazol-1-yl)propanoic acidHCID 19914606N-(3-dimethylaminopropyl)-3-(1H-imidazol-1-yl)propanamideHCID 178527764HCID 178527764, compound

Product 1

HCID 15035105N-(3-Dimethylaminopropyl)-N-(3-(1H-imidazol-1-yl)propyl)benz(cd)indol-2-amine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

3(1H-imidazol-1-yl)propanoic acid is converted to its acid chloride which upon reaction with 3-dimethylaminopropylamine leads to N-(3-dimethylaminopropyl)-3-(1H-imidazol-1-yl)propanamide. Reduction with borane in tetrahydrofuran solution then gives N-(3-dimethylaminopropyl-N-3-(1H-imidazol-1yl))propanamine. Treatment of the latter compound with molar equivalents of benz(cd)indol-2-thiol and mercuric acetate in refluxing ethanol under the conditions of Example 55 then leads to the title compound.

Sources & evidence

ORD record
ord-0057c9fc8fa04e45860934077be69dcd
Source dataset
uspto-grants-1992_01
Patent number
US05081131

Reaction notes

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