Diisopropylethylamine → 4-(6-Cyclopropyl-pyridine-2-carbonyl)-2,2-dimethyl-piperazine-1-carboxylic acid benzyl ester

HRID 334017Notes

Reaction equation

HRID 334017 reaction equation
[CH:1]1([C:4]2[N:9]=[C:8]([C:10]([OH:12])=O)[CH:7]=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.FC(F)(F)C(O)=O.[CH2:51]([O:58][C:59]([N:61]1[CH2:66][CH2:65][NH:64][CH2:63][C:62]1([CH3:68])[CH3:67])=[O:60])[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1>CN(C=O)C.O>[CH2:51]([O:58][C:59]([N:61]1[CH2:66][CH2:65][N:64]([C:10]([C:8]2[CH:7]=[CH:6][CH:5]=[C:4]([CH:1]3[CH2:2][CH2:3]3)[N:9]=2)=[O:12])[CH2:63][C:62]1([CH3:68])[CH3:67])=[O:60])[C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 824151916-Cyclopropylpicolinic acidHCID 866882432,2-Dimethyl-piperazine-1-carboxylic acid benzyl ester trifluoroacetate

Product 1

HCID 866882444-(6-Cyclopropyl-pyridine-2-carbonyl)-2,2-dimethyl-piperazine-1-carboxylic acid benzyl ester

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

200 mg (1.23 mmol) 6-cyclopropyl-pyridine-2-carboxylic acid was stirred with 450 mg (1.40 mmol) TBTU and 500 μL (2.91 mmol) DIPEA in 5.0 mL DMF at RT. After 10 min, 440 mg (1.23 mmol) 2,2-dimethyl-piperazine-1-carboxylic acid benzyl ester trifluoroacetate was added and the reaction mixture was stirred at RT over night. Water was added and the product was extracted with EtOAc. The organic layers were dried over sodium sulfate and concentrated in vacuo.

Workup

  1. extractionthe product was extracted with EtOAc
  2. dry with materialThe organic layers were dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-92ce12ddab974b9ebbd9bffa03e183d8
Source dataset
uspto-grants-2014_11
Patent number
US08883789B2

Reaction notes

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