Cyclopropylamine → 6-{[3-(3-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-amino}-pyridazine-3-carboxylic acid cyclopropylamide

HRID 548913Notes

Reaction equation

HRID 548913 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[N:8][C:9]([NH:12][CH2:13][C:14]2[C:15]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=3)=[N:16][O:17][C:18]=2[CH3:19])=[CH:10][CH:11]=1)=O)C.COC(C1N=NC(NCC2C(C3C=CC=CC=3)=NOC=2C)=CC=1)=O.[CH:51]1([NH2:54])[CH2:53][CH2:52]1>>[CH:51]1([NH:54][C:4]([C:6]2[N:7]=[N:8][C:9]([NH:12][CH2:13][C:14]3[C:15]([C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=4)=[N:16][O:17][C:18]=3[CH3:19])=[CH:10][CH:11]=2)=[O:3])[CH2:53][CH2:52]1

Participants

4

Reactant 3

HCID 69828CyclopropylamineHCID 671573116-{[3-(3-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-amino}-pyridazine-3-carboxylic acid ethyl esterHCID 671576076-[(5-Methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-pyridazine-3-carboxylic acid methyl ester

Product 1

HCID 426307396-{[3-(3-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-amino}-pyridazine-3-carboxylic acid cyclopropylamideYield 75%

Procedure

As described for example 67e, 6-{[3-(3-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-amino}-pyridazine-3-carboxylic acid ethyl ester (106 mg, 0.3 mmol) was converted, instead of 6-[(5-methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-pyridazine-3-carboxylic acid methyl ester, using cyclopropylamine instead of aminomethylcyclopropane, to the title compound (83 mg, 75%) which was obtained as a white solid. MS: m/e=368.1 [M+H]+.

Sources & evidence

ORD record
ord-f91ee8d88ecf44f292c9c007a556af28
Source dataset
uspto-grants-2011_05
Patent number
US07943619B2

Reaction notes

Loading…