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1-Methylpiperazine → 2-[5-(4-Methyl-piperazin-1-ylmethyl)-2-nitro-phenylamino]-4-(3-trifluoromethylphenyl)-thiazole-5-carboxylic acid amide

HRID 1667795
Notes
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Reaction equation

HRID 1667795 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([N+:28]([O-:30])=[O:29])=[C:7]([NH:9][C:10]2[S:11][C:12]([C:25]([NH2:27])=[O:26])=[C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=3)[N:14]=2)[CH:8]=1)=O.[CH3:31][N:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH3:31][N:32]1[CH2:37][CH2:36][N:35]([CH2:1][C:3]2[CH:4]=[CH:5][C:6]([N+:28]([O-:30])=[O:29])=[C:7]([NH:9][C:10]3[S:11][C:12]([C:25]([NH2:27])=[O:26])=[C:13]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:23])([F:22])[F:24])[CH:16]=4)[N:14]=3)[CH:8]=2)[CH2:34][CH2:33]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 866428542-(5-Formyl-2-nitro-phenylamino)-4-(3-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amide

Product 1

HCID 866428552-[5-(4-Methyl-piperazin-1-ylmethyl)-2-nitro-phenylamino]-4-(3-trifluoromethylphenyl)-thiazole-5-carboxylic acid amideYield 82.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 0.1289 g (0.295 mmole) of 2-(5-formyl-2-nitro-phenylamino)-4-(3-trifluoromethyl-phenyl)-thiazole-5-carboxylic acid amide (VI.48b), 6.5 mL of dichloromethane, 0.1 mL (0.892 mmole) of 1-methyl piperazine and 0.3321 g (1.489 mmole) of sodium triacetoxyborohydride was stirred for 16 hours. The mixture was quenched by the addition of 1 mL of saturated ammonium chloride, 1 mL of water and 5 mL of dichloromethane, followed by the addition of 10 mL of saturated sodium bicarbonate solution and 20 mL of dichloromethane. The mixture was stirred for 45 minutes and then diluted with 75 mL of dichloromethane and 5 mL of water. The aqueous layer was extracted twice with dichloromethane. The combined dichloromethane layers were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with methanol-dichloromethane (gradient 1:99-20:80) to give 0.127 g of 2-[5-(4-methyl-piperazin-1-ylmethyl)-2-nitro-phenylamino]-4-(3-trifluoromethylphenyl)-thiazole-5-carboxylic acid amide (VI.48c) as a yellow-orange solid.

Workup

  1. customThe mixture was quenched by the addition of 1 mL of saturated ammonium chloride, 1 mL of water and 5 mL of dichloromethane
  2. additionfollowed by the addition of 10 mL of saturated sodium bicarbonate solution and 20 mL of dichloromethane
  3. stirringThe mixture was stirred for 45 minutes
  4. additiondiluted with 75 mL of dichloromethane and 5 mL of water
  5. extractionThe aqueous layer was extracted twice with dichloromethane
  6. dry with materialThe combined dichloromethane layers were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel chromatography
  10. washeluting with methanol-dichloromethane (gradient 1:99-20:80)

Sources & evidence

ORD record
ord-70a299b479d840059de43f730c4d07c9
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