Diisopropylethylamine → HCID 86614929, compound

HRID 1820276Notes

Reaction equation

HRID 1820276 reaction equation
[ClH:1].[NH2:2][C@H:3]([CH:22]([CH3:24])[CH3:23])[C:4]([N:6]1[CH2:11][CH2:10][C@@:9]([C:13]2[CH:18]=[CH:17][C:16](Cl)=[CH:15][CH:14]=2)([OH:12])[C:8]([CH3:21])([CH3:20])[CH2:7]1)=[O:5].[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30](Cl)=[O:31])=[CH:28][N:27]=1.CCN(C(C)C)C(C)C>C1COCC1>[Cl:25][C:26]1[CH:34]=[CH:33][C:29]([C:30]([NH:2][C@H:3]([CH:22]([CH3:24])[CH3:23])[C:4]([N:6]2[CH2:11][CH2:10][C@:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[Cl:1])([OH:12])[C:8]([CH3:21])([CH3:20])[CH2:7]2)=[O:5])=[O:31])=[CH:28][N:27]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27821656-Chloronicotinoyl ChlorideHCID 67299922HCID 67299922, compound

Product 1

HCID 86614929HCID 86614929, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R)-2-amino-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methylbutan-1-one hydrochloride (338 mg, 0.90 mmol), THF (5 mL), and 6-chloronicotinoyl chloride (132 mg, 0.75 mmol) was cooled to 0° C. and DIPEA (233 mg, 1.80 mmol) was added dropwise. The reaction was allowed to warm to rt and stir overnight. The solvent was then removed and residue was partitioned between methylene chloride and saturated sodium bicarbonate. The layers were separated and the organic extracts were dried, filtered, and concentrated to yield 6-chloro-N—((R)-1-((S)-4-(chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-yl)nicotinamide as a white solid.

Workup

  1. customThe solvent was then removed
  2. customresidue was partitioned between methylene chloride and saturated sodium bicarbonate
  3. customThe layers were separated
  4. customthe organic extracts were dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9517b60497a147f4a51fe7e05763e085
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

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