Pyridine → HCID 178448836, compound

HRID 1090245Notes

Reaction equation

HRID 1090245 reaction equation
[CH2:1]([C:8]1[C:9]2[C:10]3[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12](S)[C:11]=3[CH:18]=[CH:19][CH:20]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=S.N1C=CC=CC=1.[N:41]1([CH:46]([CH3:50])[CH2:47][CH2:48][NH2:49])[CH:45]=[CH:44][N:43]=[CH:42]1>C(O)C>[CH2:1]([C:8]1[C:9]2[C:10]3[C:14](=[CH:15][CH:16]=1)[N:13]=[C:12]([NH:49][CH2:48][CH2:47][CH:46]([N:41]1[CH:45]=[CH:44][N:43]=[CH:42]1)[CH3:50])[C:11]=3[CH:18]=[CH:19][CH:20]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 14817Phosphorus sulfide (P2S5)HCID 139528623-(1H-Imidazol-1-yl)butan-1-amineHCID 178527781HCID 178527781, compound

Product 1

HCID 178448836HCID 178448836, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The Wolff-Kishner-Huang Minlon reductive procedure is applied to 6-benzoylbenz(cd)indol-2-one to yield 6-benzylbenz(cd)indol-2(1H)-one which is converted to 6-benzylbenz(cd)indol-2-thiol by P2S5 in refluxing pyridine. The reaction of the latter compound with 3-(1H-imidazol-1-yl)butanamine and mercuric acetate in refluxing ethanol, under the conditions of Example 55, leads to the title compound.

Sources & evidence

ORD record
ord-625c06d903114cd2bb81a45ec4b0fed9
Source dataset
uspto-grants-1992_01
Patent number
US05081131

Reaction notes

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