2-(1H-Indazol-3-yl)-1H-isoindole-1,3(2H)-dione → 1H-Indazol-3-amine, 1-(3-(1-piperidinyl)butyl)-

HRID 580176Notes

Reaction equation

HRID 580176 reaction equation
C(N(CC)CCCN1C2C(=C(Cl)C=CC=2)C(N)=N1)C.C1(=O)[N:24]([C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[NH:27][N:26]=2)C(=O)C2=CC=CC=C12.Br.[CH3:41][CH:42]([N:46]1[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1)[CH2:43][CH2:44]Br.C1(=O)N(C2C3C(=CC=CC=3Cl)NN=2)C(=O)C2=CC=CC=C12.Br.BrCCCN(CC)CC>>[N:46]1([CH:42]([CH3:41])[CH2:43][CH2:44][N:27]2[C:28]3[C:33](=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:25]([NH2:24])=[N:26]2)[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1

Participants

6

Reactant 5

HCID 27558572-(1H-Indazol-3-yl)-1H-isoindole-1,3(2H)-dioneHCID 12639158(3-Bromopropyl)diethylamine hydrobromideHCID 132293251-(3-Diethylaminopropyl)-3-amino-4-chloroindazoleHCID 132297712-(4-chloro-1H-indazol-3-yl)isoindoline-1,3-dioneHCID 201359031-(1-Methyl-3-bromopropyl)piperidine hydrobromide

Product 1

HCID 30213731H-Indazol-3-amine, 1-(3-(1-piperidinyl)butyl)-Yield 151%

Procedure

The same procedures for preparing 1-(3-diethylaminopropyl)-3-amino-4-chloroindazole as described in Example 89 were repeated except that 8 g of 3-phthalimidoindazole and 10.5 g of 1-(1-methyl-3-bromopropyl)-piperidine hydrobromide were employed instead of the 3-phthalimido-4-chloroindazole and the 3-bromopropyldiethylamine hydrobromide, respectively. As a result, 12.5 g of 1-(3-piperidinobutyl)-3-aminoindazole was obtained.

Sources & evidence

ORD record
ord-e906412d5f5a4fd788af00adb7894c7b
Source dataset
uspto-grants-1988_06
Patent number
US04751302

Reaction notes

Loading…