11-Amino-20(RS)-camptothecin → 11-Amino-20(RS)-camptothecin

HRID 330062Notes

Reaction equation

HRID 330062 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([N+:10]([O-])=O)[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:13][CH2:14][C:15]1([OH:39])[C:20](=[O:21])[O:19][CH2:18][C:17]2[C:22]([N:24]3[C:28](=[CH:29][C:16]1=2)[C:27]1[N:30]=[C:31]2[C:36](=[CH:37][C:26]=1[CH2:25]3)[CH:35]=[CH:34][C:33]([NH2:38])=[CH:32]2)=[O:23]>[Pd]>[CH3:13][CH2:14][C:15]1([OH:39])[C:20](=[O:21])[O:19][CH2:18][C:17]2[C:22]([N:24]3[C:28](=[CH:29][C:16]1=2)[C:27]1[N:30]=[C:31]2[C:36](=[CH:37][C:26]=1[CH2:25]3)[CH:35]=[CH:34][C:33]([NH2:38])=[CH:32]2)=[O:23].[NH2:1][C:2]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 2

HCID 35573311-Amino-20(RS)-camptothecinHCID 138911802-Amino-4-nitrobenzaldehyde

Product 2

HCID 35573311-Amino-20(RS)-camptothecinHCID 111477482,4-Diaminobenzaldehyde

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

In a manner similar to that described for 10-nitro-20(RS)-camptothecin, a mixture of 2-amino-4-nitrobenzaldehyde is treated with the tricyclic ketone 11 yielding 11-nitro-20(RS)-camptothecin which in turn is reduced to 11-amino-20(RS)-camptothecin by palladium/carbon. Alternatively, the 11-amino-20(RS)-camptothecin is obtained by reaction of 2,4-diaminobenzaldehyde with ketone 11.

Sources & evidence

ORD record
ord-32d81ff655774e9980f8e5eac01371d3
Source dataset
uspto-grants-1990_01
Patent number
US04894456

Reaction notes

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