Water → 3-Pyridinamine, N-(1-methylethyl)-2-(1-piperazinyl)-

HRID 2293737Notes

Reaction equation

HRID 2293737 reaction equation
CC(C)(OC([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[C:18]([NH:19][CH:20]([CH3:22])[CH3:21])=[CH:17][CH:16]=[CH:15][N:14]=2)[CH2:9][CH2:8]1)=O)C.FC(F)(F)C(O)=O.O.[OH-].[Na+]>C(Cl)Cl>[CH3:22][CH:20]([NH:19][C:18]1[C:13]([N:10]2[CH2:9][CH2:8][NH:7][CH2:12][CH2:11]2)=[N:14][CH:15]=[CH:16][CH:17]=1)[CH3:21]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acid2×HCID 14798Sodium HydroxideHCID 10448702Tert-Butyl 4-(3-(Isopropylamino)Pyridin-2-Yl)Piperazine-1-Carboxylate

Product 1

HCID 100137503-Pyridinamine, N-(1-methylethyl)-2-(1-piperazinyl)-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-[1,1-Dimethylethoxycarbonyl]-4-[3-(1-methylethylamino)-2-pyridinyl]piperazine (PREPARATION 3) is dissolved in methylene chloride (56 ml) and cooled to 0°. Then trifluoroacetic acid is added dropwise. The reaction is warmed to 20°-25° and additional trifluoroacetic acid is added (26.6 g). When the reaction is complete by TLC, it is poured into 200 ml of water and ice, basified to pH 12 with 2N aqueous sodium hydroxide, and extracted with 10% tetrahydrofuran/chloroform (2 l) followed by 10% methanol/chloroform (1 l). The organic layers are dried over anhydrous sodium sulfate, concentrated in vacuo, and used without further purification, NMR (300 MHz, CDCl3) 7.65, 6.85, 6.76, 4.16, 3.50, 2.98 and 1.20 δ.

Workup

  1. temperaturecooled to 0°
  2. temperatureThe reaction is warmed to 20°-25°
  3. extractionextracted with 10% tetrahydrofuran/chloroform (2 l)
  4. dry with materialThe organic layers are dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customused without further purification, NMR (300 MHz, CDCl3) 7.65, 6.85, 6.76, 4.16, 3.50, 2.98 and 1.20 δ

Sources & evidence

ORD record
ord-840ba33e04b14433a516984c86fa4b51
Source dataset
uspto-grants-1997_11
Patent number
US05686610

Reaction notes

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