3-Amino-4-chloroindazole → 1-(3-Morpholinopropyl)-3-amino-5-chloroindazole

HRID 580163Notes

Reaction equation

HRID 580163 reaction equation
C(N(CC)CCCN1C2C(=C(Cl)C=CC=2)C(N)=N1)C.Br.Br[CH2:22][CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.[NH2:31][C:32]1[C:40]2[C:35](=[CH:36][CH:37]=[C:38]([Cl:41])[CH:39]=2)[NH:34][N:33]=1.Br.BrCCCN(CC)CC.NC1C2C(=CC=CC=2Cl)NN=1>>[O:28]1[CH2:29][CH2:30][N:25]([CH2:24][CH2:23][CH2:22][N:34]2[C:35]3[C:40](=[CH:39][C:38]([Cl:41])=[CH:37][CH:36]=3)[C:32]([NH2:31])=[N:33]2)[CH2:26][CH2:27]1

Participants

6

Reactant 5

HCID 3134443-Amino-4-chloroindazoleHCID 12639158(3-Bromopropyl)diethylamine hydrobromideHCID 132293251-(3-Diethylaminopropyl)-3-amino-4-chloroindazoleHCID 215095384-(3-Bromopropyl)morpholine hydrobromideHCID 215161643-Amino-5-chloro-1h-indazole

Product 1

HCID 201357631-(3-Morpholinopropyl)-3-amino-5-chloroindazoleYield 110.7%

Procedure

The same procedures for preparing 1-(3-diethylaminopropyl)-3-amino-4-chloroindazole as described in Example 89 were repeated except that 5.03 g of 3-bromopropylmorpholine hydrobromide and 5.66 g of 3-amino-5-chloroindazole were employed instead of the 3-bromopropyldiethylamine hydrobromide and the 3-amino-4-chloroindazole, respectively. As a result, 5.68 g of 1-(3-morpholinopropyl)-3-amino-5-chloroindazole was obtained.

Sources & evidence

ORD record
ord-723dbef5c53241f6bbb8c7c99f023170
Source dataset
uspto-grants-1988_06
Patent number
US04751302

Reaction notes

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