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2-Furancarboxylic acid → Furan-2-carboxylic acid {7-fluoro-1-(furan-2-carbonyl)-3-[(E)-2-(pyridin-3-yl)-vinyl]-1H-indazole-5-yl}-amide

HRID 34029
Notes
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Reaction equation

HRID 34029 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH2:19])[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[C:7]2/[CH:11]=[CH:12]/[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1.[O:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[C:25]([OH:27])=O>>[F:1][C:2]1[CH:3]=[C:4]([NH:19][C:25]([C:21]2[O:20][CH:24]=[CH:23][CH:22]=2)=[O:27])[CH:5]=[C:6]2[C:10]=1[N:9]([C:25]([C:21]1[O:20][CH:24]=[CH:23][CH:22]=1)=[O:27])[N:8]=[C:7]2/[CH:11]=[CH:12]/[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 69192-Furancarboxylic acidHCID 1785078097-fluoro-3-[(E)-2-(pyridin-3-yl)-vinyl]-1H-indazol-5-ylamine

Product 1

HCID 59797182Furan-2-carboxylic acid {7-fluoro-1-(furan-2-carbonyl)-3-[(E)-2-(pyridin-3-yl)-vinyl]-1H-indazole-5-yl}-amideYield 37.9%

Procedure

Following amidation using 217 mg of 7-fluoro-3-[(E)-2-(pyridin-3-yl)-vinyl]-1H-indazol-5-ylamine and 286 mg of 2-furancarboxylic acid in accordance with the method of Example 127, purification by LC-MS was carried out, to afford 143 mg of the title compound as yellow crystals.

Workup

  1. customwith the method of Example 127, purification by LC-MS

Sources & evidence

ORD record
ord-01a90d08fb0a473ea7da21d086405516
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07429609B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes