Trifluoroacetic acid → 5-{3-[(4-Carbamimidoylphenylamino)-(6-fluoro-9-methoxy-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)methyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}-1H-pyrazole-4-carboxylic acid ethyl ester acetate

HRID 1161559Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][NH:9][C:10]=1[N:11]1[C:15](=[O:16])[NH:14][C:13]([CH:17]([C:31]2[CH:41]=[C:40]([O:42][CH3:43])[C:34]3[O:35][CH2:36][CH2:37][CH2:38][O:39][C:33]=3[C:32]=2[F:44])[NH:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[N:29]=C(C)O[N:26]=3)=[CH:21][CH:20]=2)=[N:12]1)=[O:5])[CH3:2].FC1C=C(OC)C(OC)=CC=1C(NC1C=CC(C2N=C(C)ON=2)=CC=1)C1NC(=O)N(C2C=CC=CC=2C(O)=O)N=1.FC(F)(F)C(O)=O>C(O)(=O)C>[C:4]([OH:5])(=[O:3])[CH3:6].[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][NH:9][C:10]=1[N:11]1[C:15](=[O:16])[NH:14][C:13]([CH:17]([NH:18][C:19]2[CH:20]=[CH:21][C:22]([C:25](=[NH:26])[NH2:29])=[CH:23][CH:24]=2)[C:31]2[CH:41]=[C:40]([O:42][CH3:43])[C:34]3[O:35][CH2:36][CH2:37][CH2:38][O:39][C:33]=3[C:32]=2[F:44])=[N:12]1)=[O:5])[CH3:2]

Participants

Procedure

The same procedure was carried out as in Example (1g), except that 5-(3-{(6-fluoro-9-methoxy-3,4-dihydro-2H-benzo[b][1,4]dioxepin-7-yl)-[4-(5-methyl[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)-1H-pyrazole-4-carboxylic acid ethyl ester and 0.1% acetic acid were used instead of respectively 2-(3-{(2-fluoro-4,5-dimethoxyphenyl)-[4-(5-methyl-[1,2,4]oxadiazol-3-yl)phenylamino]methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)benzoic acid and 0.1% trifluoroacetic acid, to give the title compound as a light yellow solid.

Sources & evidence

ORD record: ord-c053453840674fe8b859296dd8902ce0
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816522B2

Reaction notes

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Reaction equation

Participants

Reactant 3

Product 1

Reagents, catalysts & solvents 1

Procedure

Sources & evidence

Reaction notes