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Formic Acid → 2-[6-(4-Methyl-piperazin-1-ylmethyl)-benzoimidazol-1-yl]-4-(4-trifluoromethyl-phenyl)thiazole-5-carboxylic acid amide trifluoroacetic acid salt

HRID 1667792
Notes
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Reaction equation

HRID 1667792 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]([N+:34]([O-])=O)=[C:13]([NH:15][C:16]3[S:17][C:18]([C:31]([NH2:33])=[O:32])=[C:19]([C:21]4[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=4)[N:20]=3)[CH:14]=2)[CH2:4][CH2:3]1.[H][H].[CH:39]([OH:41])=[O:40]>[Pd]>[F:28][C:27]([F:30])([F:29])[C:39]([OH:41])=[O:40].[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[CH:11][C:12]3[N:34]=[CH:39][N:15]([C:16]4[S:17][C:18]([C:31]([NH2:33])=[O:32])=[C:19]([C:21]5[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=5)[N:20]=4)[C:13]=3[CH:14]=2)[CH2:4][CH2:3]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 284Formic AcidHCID 866428512-[5-(4-Methyl-piperazin-1-ylmethyl)-2-nitro-phenylamino]-4-(4-trifluoromethyl-phenyl)thiazole-5-carboxylic acid amideHCID 178418361HCID 178418361, compound

Product 1

HCID 866428522-[6-(4-Methyl-piperazin-1-ylmethyl)-benzoimidazol-1-yl]-4-(4-trifluoromethyl-phenyl)thiazole-5-carboxylic acid amide trifluoroacetic acid salt

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of 0.072 g (0.138 mmole) of 2-[5-(4-methyl-piperazin-1-ylmethyl)-2-nitro-phenylamino]-4-(4-trifluoromethyl-phenyl)thiazole-5-carboxylic acid amide (VI.47c), 0.0696 g of 10% palladium on carbon catalyst, and 6 mL of 96% formic acid was stirred under one atmosphere of hydrogen for 17 hours. The mixture was filtered through Diatomaceous earth and the filter pad was washed with tetrahydrofuran. The filtrate was concentrated under reduced pressure. The residue was purified by reverse phase silica gel chromatography, eluting with acetonitrile-water-trifluoroacetic acid (gradient 10:90:0.1-60:40:0.1) to give 2-[6-(4-methyl-piperazin-1-ylmethyl)-benzoimidazol-1-yl]-4-(4-trifluoromethyl-phenyl)thiazole-5-carboxylic acid amide trifluoroacetic acid salt (I.47a). This salt was partitioned between 10 mL of saturated sodium carbonate solution and 150 mL of ethyl acetate. The organic layer was washed with 15 mL of water, then 15 mL of brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 0.0401 g of 2-[6-(4-methyl-piperazin-1-ylmethyl)-benzoimidazol-1-yl]-4-(4-trifluoromethyl-phenyl)thiazole-5-carboxylic acid amide (I.47) as a white solid. MH+/Z=501.

Workup

  1. filtrationThe mixture was filtered through Diatomaceous earth
  2. washthe filter pad was washed with tetrahydrofuran
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by reverse phase silica gel chromatography
  5. washeluting with acetonitrile-water-trifluoroacetic acid (gradient 10:90:0.1-60:40:0.1)

Sources & evidence

ORD record
ord-1d64cce5f8fb4b12abc716fc1c8cd449
Source dataset
uspto-grants-2011_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08044213B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes