Ammonium Chloride → HCID 67920597, compound

HRID 704087Notes

Reaction equation

Cl[C:2]1[C:7]2[CH:8]=[C:9]3[N:14]([C:6]=2[C:5]([CH3:15])=[N:4][N:3]=1)[CH:13]=[CH:12][CH:11]=[CH:10]3.[N:16]1([CH2:21][CH2:22][CH2:23]N)[CH:20]=[CH:19][N:18]=[CH:17]1.[Cl-].[NH4+]>>[CH3:15][C:5]1[C:6]2[N:14]3[C:9]([CH:10]=[CH:11][CH:12]=[CH:13]3)=[CH:8][C:7]=2[CH2:2][N:3]([CH2:23][CH2:22][CH2:21][N:16]2[CH:20]=[CH:19][N:18]=[CH:17]2)[N:4]=1

Participants

Reactant 3

HCID 25517Ammonium Chloride

HCID 787361H-Imidazole-1-propanamine

HCID 157133121-Chloro-4-methylpyridazino[4,5-b]indolizine

Product 1

HCID 67920597HCID 67920597, compound

Procedure

Following the procedure of Example 1, reaction of one equivalent of 1-chloro-4-methylpyridazino[4,5-b]indolizine, eight equivalents of 3-(1H-imidazol-1-yl)propylamine and one equivalent of ammonium chloride under reflux in a nitrogen atmosphere for 1 hour and at room temperature for 48 hours gave the title compound as the free base after removal of excess amine in vacuo and purification by flash chromatography (silica gel, 10 to 40% methanol in ethyl acetate). The free base was converted to the dihydrochloride salt (methanol/ethereal HCl/diethyl ether), mp 162°-163° C.

Sources & evidence

ORD record: ord-1ea4201d1ea64082b3633bbabc58f219
Source dataset: uspto-grants-1991_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04985560

Reaction notes

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