1-Hydroxybenzotriazole → 1-(tert-Butoxycarbonyl)-4-[4-methyl-2-(4-pyridyl)-5-thiazolecarbonyl]piperazine

HRID 278569Notes

Reaction equation

HRID 278569 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:14][C:15]1[N:16]=[C:17]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)[S:18][C:19]=1[C:20](O)=[O:21].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl>CN(C=O)C.C(N(CC)CC)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:20]([C:19]2[S:18][C:17]([C:23]3[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=3)=[N:16][C:15]=2[CH3:14])=[O:21])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 757711-HydroxybenzotriazoleHCID 143452tert-Butyl piperazine-1-carboxylateHCID 14837132-(4-Pyridyl)-4-methylthiazole-5-carboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 226279351-(tert-Butoxycarbonyl)-4-[4-methyl-2-(4-pyridyl)-5-thiazolecarbonyl]piperazineYield 83.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 1-(tert-butoxycarbonyl)piperazine (3.72 g), 4-methyl-2-(4-pyridyl) -5-thiazolecarboxylic acid (4.4 g), triethylamine (2.5 g) and HOBt (2.7 g) in DMF (60 ml), was added WSC hydrochloride (4.217 g) under ice-cooling and the mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated, and to the residue were added dichloromethane and sodium bicarbonate aqueous solution. The organic layer was separated, washed with water and brine, dried and concentrated. The residue was purified with silica gel chromatography (dichloromethane:methanol=50:1) to give colorless crystals of the title compound (6.49 g).

Workup

  1. temperaturecooling
  2. concentrationThe reaction solution was concentrated
  3. additionto the residue were added dichloromethane and sodium bicarbonate aqueous solution
  4. customThe organic layer was separated
  5. washwashed with water and brine
  6. customdried
  7. concentrationconcentrated
  8. customThe residue was purified with silica gel chromatography (dichloromethane:methanol=50:1)

Sources & evidence

ORD record
ord-4f931e0184544f0a9af673cd3fc97461
Source dataset
uspto-grants-2002_03
Patent number
US06359134B1

Reaction notes

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