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

HRID 1520269Notes

Reaction equation

HRID 1520269 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([NH:21][C:22]3[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=3)[CH2:15][CH2:16][C:17]([F:20])([F:19])[F:18])=[C:10]([CH3:31])[CH:9]=2)=[N:6][CH:7]=1.[NH:32]1[CH2:37][CH2:36][CH2:35][C@@H:34]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:33]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>[Cl:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH:14]([NH:21][C:22]3[CH:23]=[CH:24][C:25]([C:26]([N:32]4[CH2:37][CH2:36][CH2:35][C@@H:34]([C:38]([O:40][CH2:41][CH3:42])=[O:39])[CH2:33]4)=[O:27])=[CH:29][CH:30]=3)[CH2:15][CH2:16][C:17]([F:19])([F:18])[F:20])=[C:10]([CH3:31])[CH:9]=2)=[N:4][CH:3]=1

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 185582ethyl (3R)-piperidine-3-carboxylateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 1178403514-((1-(4-(5-Chloropyrimidin-2-yl)-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoic acid

Product 1

HCID 131733099ethyl (3R)-1-(4-((1-(4-(5-chloropyrimidin-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-chloropyrimidin-2-yl)-2-methylphenyl)-4,4,4-trifluorobutyl)amino)benzoic acid (0.407 g), ethyl (3R)-piperidine-3-carboxylate (0.153 mL), 1-hydroxybenzotriazole monohydrate (0.152 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.191 g) and diisopropylethylamine (0.174 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 (0.419 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-9bc1a5cf21444a09a88120c76d3e67e8
Source dataset
uspto-grants-2015_07
Patent number
US09073864B2

Reaction notes

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