Diisopropylethylamine → HCID 66817124, compound

HRID 1754914Notes

Reaction equation

HRID 1754914 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[C:34]([O:38][C:39]([N:41]1[CH2:46][CH2:45][C:44]([NH2:50])([C:47](=[O:49])[NH2:48])[CH2:43][CH2:42]1)=[O:40])([CH3:37])([CH3:36])[CH3:35].[F:51][C:52]1[CH:60]=[C:59]([C:61]([F:64])([F:63])[F:62])[CH:58]=[CH:57][C:53]=1[C:54](O)=[O:55]>CN(C=O)C>[C:34]([O:38][C:39]([N:41]1[CH2:42][CH2:43][C:44]([C:47](=[O:49])[NH2:48])([NH:50][C:54](=[O:55])[C:53]2[CH:57]=[CH:58][C:59]([C:61]([F:62])([F:63])[F:64])=[CH:60][C:52]=2[F:51])[CH2:45][CH2:46]1)=[O:40])([CH3:37])([CH3:35])[CH3:36]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5180032-Fluoro-4-(trifluoromethyl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10562199tert-Butyl 4-amino-4-carbamoylpiperidine-1-carboxylate

Product 1

HCID 66817124HCID 66817124, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (939 mg, 2.47 mmol) and DIPEA (525 μL, 3.09 mmol) were added to a solution of 4-amino-4-carbamoyl-piperidine-1-carboxylic acid tert-butyl ester (500 mg, 2.06 mmol) and 2-fluoro-4-trifluoromethyl-benzoic acid (514 mg, 2.47 mmol) in DMF (10 mL). The mixture was stirred at room temperature for 19 hours and then quenched with a saturated aqueous ammonium chloride solution. The reaction mixture was diluted with EtOAc, and the organic layer was then washed with H2O and saturated brine, dried over MgSO4 and concentrated under reduced pressure. The resulting residue was triturated with n-hexane and EtOAc and then collected by filtration to give 4-carbamoyl-4-(2-fluoro-4-trifluoromethyl-benzoylamino)-piperidine-1-carboxylic acid tert-butyl ester as a white solid. This was used in the next step without further purification.

Workup

  1. customquenched with a saturated aqueous ammonium chloride solution
  2. additionThe reaction mixture was diluted with EtOAc
  3. washthe organic layer was then washed with H2O and saturated brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was triturated with n-hexane and EtOAc
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-c4df05d6069349b4b43cec6b75c6eb06
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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