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1-Isopropylpiperazine → HCID 57618998, compound

HRID 561081
Notes
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Reaction equation

HRID 561081 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5](/[CH:7]=[CH:8]/[C:9]([OH:11])=O)[CH:4]=[N:3]1.[CH:12]([N:15]1[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]1)([CH3:14])[CH3:13].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.C([O-])(O)=O.[Na+]>[CH:12]([N:15]1[CH2:20][CH2:19][N:18]([C:9](=[O:11])/[CH:8]=[CH:7]/[C:5]2[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=2)[CH2:17][CH2:16]1)([CH3:14])[CH3:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 780131-IsopropylpiperazineHCID 1529858(2E)-3-(1-methyl-1H-pyrazol-4-yl)prop-2-enoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 57618998HCID 57618998, compoundYield 48.3%

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 516892Sodium BicarbonateSolvent

Procedure

(E)-3-(1-methyl-1H-pyrazol-4-yl)acrylic acid (913 mg, 6.00 mmol) and 1-isopropylpiperazine (1539 mg, 12.00 mmol) were dissolved in anhydrous DMF (12 mL) then HATU (2282 mg, 6.00 mmol) was added and the resulting reaction mixture was stirred over night at RT. The reaction mixture was diluted with concentrated aq. NaHCO3 and extracted with EtOAc (4×80 ml). The organic phases were combined, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give 760 mg 45A (48.3% yield) as a yellow oil residue. 45A was used directly in the next step with out further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.97 (d, J=6.64 Hz, 6H) 2.42 (br. s., 4H) 2.63-2.75 (m, 1H) 3.60 (br. s., 5H) 3.82 (s, 4H) 6.92 (d, J=15.23 Hz, 1H) 7.36 (d, J=15.23 Hz, 1H) 7.84 (s, 1H) 8.03 (s, 1H), ES[M+H]+=263.26

Workup

  1. customthe resulting reaction mixture
  2. extractionextracted with EtOAc (4×80 ml)
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7485cc4c9e624a0695292f8ce72f4cf3
Source dataset
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08063215B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes