Water → HCID 86685837, compound

HRID 1045805Notes

Reaction equation

HRID 1045805 reaction equation
Cl.[F:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[C@@H:10]1[CH2:14][NH:13][CH2:12][C@H:11]1[C:15]([O:17][CH3:18])=[O:16].[Cl:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22](Cl)[N:21]=1.C(N(C(C)C)CC)(C)C.O>CN1C(=O)CCC1>[Cl:19][C:20]1[N:21]=[C:22]([N:13]2[CH2:14][C@@H:10]([C:4]3[CH:5]=[CH:6][C:7]([F:9])=[CH:8][C:3]=3[F:2])[C@H:11]([C:15]([O:17][CH3:18])=[O:16])[CH2:12]2)[CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 169892,6-DichloropyridineHCID 81531DiisopropylethylamineHCID 86685838HCID 86685838, compound

Product 1

HCID 86685837HCID 86685837, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Methyl (3S,4R)-4-(2,4-difluorophenyl)pyrrolidine-3-carboxylate hydrochloride (prepared according to Young, J. R. et. al. Bioorganic and Medicinal Chemistry Letters 2007, 17, 5310-5315; 100 mg, 0.360 mmol), 2,6-dichloropyridine (107 mg, 0.720 mmol) and N,N-diisopropyl-N-ethylamine (0.189 ml, 1.080 mmol) in NMP (2.0 ml) was heated by microwave (150° C., 30 min). The mixture was cooled to rt, poured into water and extracted with MTBE. Purification on SiO2 (0 to 30% EtOAc, hexanes) afforded the title compound. HPLC/MS: 353.1/354.9 (M+1); Rt=1.22 min (LC2).

Workup

  1. extractionextracted with MTBE
  2. customPurification on SiO2 (0 to 30% EtOAc, hexanes)

Sources & evidence

ORD record
ord-34da9e9574324fcc8b58957bbeb8cb56
Source dataset
uspto-grants-2013_10
Patent number
US08569299B2

Reaction notes

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