Diisopropylethylamine → ethyl (3R)-1-(4-((1-(4-(5-ethylpyrimidin-2-yl)-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoyl)piperidine-3-carboxylate

HRID 1520273Notes

Reaction equation

HRID 1520273 reaction equation
[CH2:1]([C:3]1[CH:4]=[N:5][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]([NH:22][C:23]3[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][CH:24]=3)[CH2:16][CH2:17][C:18]([F:21])([F:20])[F:19])=[C:11]([CH3:32])[CH:10]=2)=[N:7][CH:8]=1)[CH3:2].[NH:33]1[CH2:38][CH2:37][CH2:36][C@@H:35]([C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH2:34]1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(N(C(C)C)CC)(C)C>CN(C)C=O.O>[CH2:1]([C:3]1[CH:8]=[N:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH:15]([NH:22][C:23]3[CH:24]=[CH:25][C:26]([C:27]([N:33]4[CH2:38][CH2:37][CH2:36][C@@H:35]([C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH2:34]4)=[O:28])=[CH:30][CH:31]=3)[CH2:16][CH2:17][C:18]([F:20])([F:21])[F:19])=[C:11]([CH3:32])[CH:10]=2)=[N:5][CH:4]=1)[CH3:2]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 185582ethyl (3R)-piperidine-3-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 1178400304-((1-(4-(5-Ethylpyrimidin-2-yl)-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoic acid

Product 1

HCID 131733101ethyl (3R)-1-(4-((1-(4-(5-ethylpyrimidin-2-yl)-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoyl)piperidine-3-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-((1-(4-(5-ethylpyrimidin-2-yl)-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoic acid, ethyl (3R)-piperidine-3-carboxylate (0.186 mL), 1-hydroxybenzotriazole monohydrate (0.185 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.231 g) and diisopropylethylamine (0.211 mL) in dimethylformamide (3 mL) was stirred at room temperature overnight. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (0.574 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-73413bb5fd7043f89a42cb7bd912abaf
Source dataset
uspto-grants-2015_07
Patent number
US09073864B2

Reaction notes

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