6-[(5-Methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-pyridazine-3-carboxylic acid methyl ester → 6-{[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-amino}-pyridazine-3-carboxylic acid cyclopropylmethyl-amide

HRID 548883Notes

Reaction equation

HRID 548883 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][C:23]([F:26])=[CH:22][CH:21]=3)=[N:16][O:17][C:18]=2[CH3:19])=[CH:10][CH:11]=1)=O)C.COC(C1N=NC(NCC2[C:40]([C:45]3[CH:50]=[CH:49]C=CC=3)=[N:41]OC=2C)=CC=1)=O>>[CH:45]1([CH2:40][NH:41][C:4]([C:6]2[N:7]=[N:8][C:9]([NH:12][CH2:13][C:14]3[C:15]([C:20]4[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=4)=[N:16][O:17][C:18]=3[CH3:19])=[CH:10][CH:11]=2)=[O:3])[CH2:50][CH2:49]1

Participants

3

Reactant 2

HCID 671576076-[(5-Methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-pyridazine-3-carboxylic acid methyl esterHCID 671578636-{[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-amino}-pyridazine-3-carboxylic acid ethyl ester

Product 1

HCID 671578796-{[3-(4-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-amino}-pyridazine-3-carboxylic acid cyclopropylmethyl-amideYield 91%

Procedure

As described for example 73c, 6-{[3-(4-fluoro-phenyl)-5-methyl-isoxazol-4-ylmethyl]-amino}-pyridazine-3-carboxylic acid ethyl ester (89 mg, 0.25 mmol) was converted, instead of 6-[(5-methyl-3-phenyl-isoxazol-4-ylmethyl)-amino]-pyridazine-3-carboxylic acid methyl ester, to the title compound (87 mg, 91%) which was obtained as an off white foam. MS: m/e=382.4 [M+H]+.

Sources & evidence

ORD record
ord-f5c11bff4ef94e6b8fdc62130eb55847
Source dataset
uspto-grants-2011_05
Patent number
US07943619B2

Reaction notes

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