1-Methylpiperazine → HCID 86642826, compound

HRID 1667716Notes

Reaction equation

HRID 1667716 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([NH:16][C:17]2[CH:22]=[C:21]([CH:23]=O)[CH:20]=[CH:19][C:18]=2[N+:25]([O-:27])=[O:26])[S:11][C:12]=1[C:13]([NH2:15])=[O:14].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:42][N:43]1[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]1>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[C:10]([NH:16][C:17]2[CH:22]=[C:21]([CH2:23][N:46]3[CH2:47][CH2:48][N:43]([CH3:42])[CH2:44][CH2:45]3)[CH:20]=[CH:19][C:18]=2[N+:25]([O-:27])=[O:26])[S:11][C:12]=1[C:13]([NH2:15])=[O:14]

Participants

5

Reactant 3

HCID 531671-MethylpiperazineHCID 5049666Sodium triacetoxyborohydrideHCID 86642827HCID 86642827, compound

Product 1

HCID 86642826HCID 86642826, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 0.20 g (0.50 mmole) of 4-(2-chloro-phenyl)-2-(5-formyl-2-nitro-phenylamino)-thiazole-5-carboxylic acid amide (VI.20b), 0.63 g (3.0 mmole) of sodium triacetoxyborohydride and 15 mL of dichloromethane was added 0.12 mL (1.08 mmole) of 1-methylpiperazine. The mixture was stirred at room temperature for 3 days. The mixture was diluted with dichloromethane, washed with saturated aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with methanol-dichloromethane (gradient 0:100-15:85) to give 0.20 g of 4-(2-chloro-phenyl)-2-[5-(4-methyl-piperazin-1-ylmethyl)-2-nitro-phenylamino]-thiazole-5-carboxylic acid amide (VI.20c).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with methanol-dichloromethane (gradient 0:100-15:85)

Sources & evidence

ORD record
ord-386c1fb6d5714418962a8473c1800ddd
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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