1-Isopropylpiperazine → HCID 68731520, compound

HRID 1970961Notes

Reaction equation

HRID 1970961 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([B:10]([OH:12])[OH:11])=[CH:6][CH:5]=1)([OH:3])=O.[CH:13]([N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)([CH3:15])[CH3:14].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH:13]([N:16]1[CH2:21][CH2:20][N:19]([C:1]([C:4]2[CH:9]=[CH:8][C:7]([B:10]([OH:12])[OH:11])=[CH:6][CH:5]=2)=[O:3])[CH2:18][CH2:17]1)([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 780131-IsopropylpiperazineHCID 3121834-Carboxyphenylboronic 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 68731520HCID 68731520, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-carboxyphenylboronic acid (1 eq, 213 mg) in DMF (5 ml) is treated with 1-isopropylpiperazine (1 eq, 155 mg) and the reaction mixture is stirred at RT for 10 minutes. TEA (1.2 eq, 0.202 ml) and HATU (2.4 eq, 1.104 g) are added and the resulting mixture is stirred at RT overnight. The reaction is quenched by addition of water and the mixture is extracted with DCM (2×). The combined organic portions are washed with brine, dried (MgSO4) and concentrated in vacuo. The residue is dried in vacuo at 50° C. overnight to afford the title compound which is used without further purification [M+H]+=277

Workup

  1. stirringthe resulting mixture is stirred at RT overnight
  2. customThe reaction is quenched by addition of water
  3. extractionthe mixture is extracted with DCM (2×)
  4. washThe combined organic portions are washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue is dried in vacuo at 50° C. overnight

Sources & evidence

ORD record
ord-ac17b8b71f324e5db70a3ff24a5d1e70
Source dataset
uspto-grants-2013_04
Patent number
US08431578B2

Reaction notes

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