Isopropylamine → HCID 21041189, compound

HRID 10292Notes

Reaction equation

HRID 10292 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[C:5]1[CH:10]=[C:9]([F:11])[C:8]([N:12]2[CH2:16][CH2:15][CH:14]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]2)=[CH:7][C:6]=1F)[CH3:2].[CH:27]([NH2:30])([CH3:29])[CH3:28]>CS(C)=O>[CH2:1]([O:3][C:4](=[O:26])[C:5]1[CH:10]=[C:9]([F:11])[C:8]([N:12]2[CH2:16][CH2:15][CH:14]([NH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]2)=[CH:7][C:6]=1[NH:30][CH:27]([CH3:29])[CH3:28])[CH3:2]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 690751024-(3-tert-Butoxycarbonylaminopyrrolidin-1-yl)-2,5-difluorobenzoic acid ethyl ester

Product 1

HCID 21041189HCID 21041189, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4-[3-(tert-Butoxycarbonylamino)-pyrrolidin-1-yl]-2,5-difluorobenzoic acid ethyl ester (Example 2j, 5.4 g, 13.9 mmol), isopropylamine (40 mL, 469 mmol), and dimethyl sulfoxide (25 mL) are heated at 100° C. for 4 days in a sealed glass tube. The excess amine is removed by blowing in compressed air. The residue is filtered and concentrated under vacuum to a thick oil. Purification by column chromatography (1:1:7 ethyl acetate/chloroform/hexanes) to provide the title compound as a solid (1.6 g). MS: m/z 410 (MH+).

Workup

  1. customThe excess amine is removed
  2. filtrationThe residue is filtered
  3. concentrationconcentrated under vacuum to a thick oil
  4. customPurification by column chromatography (1:1:7 ethyl acetate/chloroform/hexanes)

Sources & evidence

ORD record
ord-f10a2f09cda54566ab1f1c06aa827088
Source dataset
uspto-grants-2006_08
Patent number
US07094780B1

Reaction notes

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