2,5-Hexanedione → N-({1-[4-(2,5-Dimethyl-pyrrol-1-yl)-cyclohexyl]-azetidin-3-ylcarbamoyl}-methyl)-3-trifluoromethyl-benzamide

HRID 2188585Notes

Reaction equation

HRID 2188585 reaction equation
OC(C(F)(F)F)=O.[NH2:8][CH:9]1[CH2:14][CH2:13][CH:12]([N:15]2[CH2:18][CH:17]([NH:19][C:20]([CH2:22][NH:23][C:24](=[O:35])[C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=3)=[O:21])[CH2:16]2)[CH2:11][CH2:10]1.CCN(C(C)C)C(C)C.[CH2:45]([CH2:49][C:50](=O)[CH3:51])[C:46]([CH3:48])=O>CO>[CH3:51][C:50]1[N:8]([CH:9]2[CH2:10][CH2:11][CH:12]([N:15]3[CH2:18][CH:17]([NH:19][C:20]([CH2:22][NH:23][C:24](=[O:35])[C:25]4[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:32])([F:33])[F:34])[CH:26]=4)=[O:21])[CH2:16]3)[CH2:13][CH2:14]2)[C:46]([CH3:48])=[CH:45][CH:49]=1

Participants

5

Reactant 3

HCID 80352,5-HexanedioneHCID 81531DiisopropylethylamineHCID 86646662N-{[1-(4-Amino-cyclohexyl)-azetidin-3-ylcarbamoyl]-methyl}-3-trifluoromethyl-benzamide TFA salt

Product 1

HCID 49763450N-({1-[4-(2,5-Dimethyl-pyrrol-1-yl)-cyclohexyl]-azetidin-3-ylcarbamoyl}-methyl)-3-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-{[1-(4-amino-cyclohexyl)-azetidin-3-ylcarbamoyl]-methyl}-3-trifluoromethyl-benzamide trifluoroacetic acid salt (as prepared in Example 35 Step B, 0.24 g, 0.4 mmol) in methanol (2 mL) was added DIEA (Aldrich, 0.21 mL, 1.2 mmol) and acetonylacetone (Aldrich, 0.06 mL, 0.5 mmol). The resulting mixture was stirred at rt overnight and the volatile organics were removed by evaporation. The residue was dissolved in water, extracted with EtOAc, dried over Na2SO4. Filtration and evaporation gave a crude product, which was purified by column chromatography (eluent: EtOAc) to give the cis isomer as a white solid.

Workup

  1. customthe volatile organics were removed by evaporation
  2. dissolutionThe residue was dissolved in water
  3. extractionextracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-9dc4365154694580964d35faf067200e
Source dataset
uspto-grants-2012_12
Patent number
US08324186B2

Reaction notes

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