Diisopropylethylamine → HCID 9977220, compound

HRID 347661Notes

Reaction equation

HRID 347661 reaction equation
[I:1][C:2]1[CH:3]=[N:4][N:5]([C:7]([O:9]C2C=CC=CC=2)=O)[CH:6]=1.[ClH:16].Cl.[NH2:18][C@@H:19]1[CH:24]2[CH2:25][CH2:26][N:21]([CH2:22][CH2:23]2)[CH2:20]1.CCN(C(C)C)C(C)C>CN(C=O)C>[ClH:16].[N:21]12[CH2:26][CH2:25][CH:24]([CH2:23][CH2:22]1)[C@@H:19]([NH:18][C:7]([N:5]1[CH:6]=[C:2]([I:1])[CH:3]=[N:4]1)=[O:9])[CH2:20]2

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 12494972(R)-(+)-3-Aminoquinuclidine DihydrochlorideHCID 21083552HCID 21083552, compound

Product 1

HCID 9977220HCID 9977220, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Phenyl 4-iodo-1H-pyrazole-1-carboxylate (1.6 g, 5.2 mmol) and (R)-(+)-3-aminoquinuclidine dihydrochloride (1.0 g, 5.2 mmol) are suspended in 10 mL DMF. DIEA (2.7 mL, 15.5 mmol) is added dropwise. After 36 h, the solvent is removed and the residue is taken up in 1N NaOH and CHCl3. The aqueous layer is extracted with CHCl3, dried (MgSO4), filtered and concentrated. The residue is purified by chromatography (Biotage 40S, 90:9:1 CHCl3/MeOH/NH4OH) to provide 1.66 g (93%) of the product as a white solid. A portion of the material is converted into the hydrochloride salt and recrystallized from MeOH/EtOAc. HRMS (FAB) calcd for C11H15IN4O+H 347.0370, found 347.0357.

Workup

  1. customthe solvent is removed
  2. extractionThe aqueous layer is extracted with CHCl3
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue is purified by chromatography (Biotage 40S, 90:9:1 CHCl3/MeOH/NH4OH)

Sources & evidence

ORD record
ord-1032ff07715e4c42a61964de3f6a0148
Source dataset
uspto-grants-2007_02
Patent number
US07176198B2

Reaction notes

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