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5-Chlorofuran-2-carboxylic acid → N1-(5-Chlorofuran-2-ylcarbonyl)-N2-[1-(4-pyridyl)piperidin-4-ylmethoxycarbonyl]-1,2-benzenediamine Hydrochloride

HRID 395819
Notes
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Reaction equation

HRID 395819 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]([CH:19]2[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]2)[O:8][C:9]([NH:11][C:12]2[C:13]([NH2:18])=[CH:14][CH:15]=[CH:16][CH:17]=2)=[O:10])=[CH:3][CH:2]=1.[Cl:25][C:26]1[O:30][C:29]([C:31](O)=[O:32])=[CH:28][CH:27]=1>>[ClH:25].[Cl:25][C:26]1[O:30][C:29]([C:31]([NH:18][C:13]2[C:12]([NH:11][C:9]([O:8][CH:7]([CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)[C:4]3[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=3)=[O:10])=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:32])=[CH:28][CH:27]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 2348535-Chlorofuran-2-carboxylic acidHCID 86585755N1-[1-(4-pyridyl)piperidin-4-ylmethoxycarbonyl)-1,2-benzenediamine

Product 1

HCID 86585766N1-(5-Chlorofuran-2-ylcarbonyl)-N2-[1-(4-pyridyl)piperidin-4-ylmethoxycarbonyl]-1,2-benzenediamine HydrochlorideYield 22%

Procedure

Using the procedure described in Example 168, N1-[1-(4-pyridyl)piperidin-4-ylmethoxycarbonyl]-1,2-benzenediamine (0.61 mmol) and 5-chloro-2-furancarboxylic acid (1.2 mmol), purifying with RPHPLC Method A, yielded 57 mg (22%) of the title compound.

Workup

  1. custompurifying with RPHPLC Method A

Sources & evidence

ORD record
ord-f4fd0a8ff60e4cdc9c2aaeab370ef6ef
Source dataset
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06605626B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes