1H-indazol-3-amine → 1-[3-(Morpholin-4-yl)butyl]-1H-indazol-3-amine

HRID 484909Notes

Reaction equation

HRID 484909 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][N:3]=1.Br.[CH3:12][CH:13]([N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1)[CH2:14][CH2:15]Br.NC1C2C(=CC=CC=2Cl)NN=1.Br.BrCCCN(CC)CC>>[O:20]1[CH2:21][CH2:22][N:17]([CH:13]([CH3:12])[CH2:14][CH2:15][N:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:2]([NH2:1])=[N:3]2)[CH2:18][CH2:19]1

Participants

5

Reactant 4

HCID 133991H-indazol-3-amineHCID 3134443-Amino-4-chloroindazoleHCID 12639158(3-Bromopropyl)diethylamine hydrobromideHCID 703527374-(4-Bromobutan-2-yl)morpholine--hydrogen bromide (1/1)

Product 1

HCID 132105801-[3-(Morpholin-4-yl)butyl]-1H-indazol-3-amineYield 48%

Procedure

The same procedures as described in Example 1 were repeated except that 4.50 g of 3-aminoindazole and 5.03 g of (1-methyl-3-bromopropyl)-morpholine hydrobromide were employed instead of the 5.66 g of 3-amino-4-chloroindazole and the 4.83 g of 3-bromopropyldiethylamine hydrobromide, respectively. As a result, 1-(3-morpholinobutyl)-3-aminoindazole having the following analytical values was obtained in a yield of 48%.

Sources & evidence

ORD record
ord-3ab88c255aef4b8d8aa2545d9343cb02
Source dataset
uspto-grants-1985_08
Patent number
US04533731

Reaction notes

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