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Diisopropylethylamine → HCID 86688251, compound

HRID 334020
Notes
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Reaction equation

HRID 334020 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]([OH:11])=O)[CH:6]=[CH:5][CH:4]=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.[CH2:50]([O:57][C:58]([N:60]1[CH2:65][CH2:64][NH:63][CH2:62][C:61]1([CH3:67])[CH3:66])=[O:59])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>C(Cl)Cl>[CH2:50]([O:57][C:58]([N:60]1[CH2:65][CH2:64][N:63]([C:9]([C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[N:8]=2)=[O:11])[CH2:62][C:61]1([CH3:67])[CH3:66])=[O:59])[C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5708916-Methoxypicolinic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 866882432,2-Dimethyl-piperazine-1-carboxylic acid benzyl ester trifluoroacetate

Product 1

HCID 86688251HCID 86688251, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

510 mg (3.31 mmol) 6-methoxy-2-pyridinecarboxylic acid was stirred with 1.17 g (3.31 mmol) TBTU and 1.50 mL (8.72 mmol) DIPEA in 10 mL DCM at RT. After 10 min, 1.20 g (3.31 mmol) 2,2-dimethyl-piperazine-1-carboxylic acid benzyl ester trifluoroacetate was added and the reaction mixture was stirred at RT for 2 h. Then the reaction mixture was washed with saturated aqueous NaHCO3 solution. The combined organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by flash chromatography (PE/EtOAc=9/1→1/2).

Workup

  1. washThen the reaction mixture was washed with saturated aqueous NaHCO3 solution
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe crude material was purified by flash chromatography (PE/EtOAc=9/1→1/2)

Sources & evidence

ORD record
ord-4da99b73ff814972b94d4414e9eb1435
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08883789B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes