Triethylamine → HCID 10246820, compound

HRID 1823070Notes

Reaction equation

HRID 1823070 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][O:7][C:8]2[N:13]=[CH:12][C:11]([N:14]3[C:18](=[O:19])[CH2:17][CH:16]([C:20]([OH:22])=O)[CH2:15]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl.CN.[CH2:28]([N:30](CC)CC)C>CN(C)C=O>[CH3:28][NH:30][C:20]([CH:16]1[CH2:17][C:18](=[O:19])[N:14]([C:11]2[CH:12]=[N:13][C:8]([O:7][CH2:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:24][CH:23]=3)=[CH:9][CH:10]=2)[CH2:15]1)=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 6364545Methylamine hydrochlorideHCID 21920059HCID 21920059, compound

Product 1

HCID 10246820HCID 10246820, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 105 mg (0.3 mmol) of (RS)-1-[6-(4-fluoro-benzyloxy)-pyridin-3-yl]-5-oxo-pyrrolidine-3-carboxylic acid in 5 ml N,N-dimethylformamide is treated with 58 mg (0.35 mmol) of N,N-carbonyl-diimidazole, and the mixture is stirred at RT for 15 min. Thereafter, 26 mg (0.38 mmol) of methylamine hydrochloride and 50 μl (0.35 mmol) of triethylamine are added. After 30 min, the solvent is evaporated under reduced pressure and the residue is chromatographed on silica gel using a 98:2-mixture of dichloromethane and methanol as the eluent. There are obtained 15 mg (15% of theory) of (RS)-1-[6-(4-fluoro-benzyloxy)-pyridin-3-yl]-5-oxo-pyrrolidine-3-carboxylic acid methylamide as a green oil which solidifies on standing. MS: m/e=344 (M+H)+.

Workup

  1. waitAfter 30 min
  2. customthe solvent is evaporated under reduced pressure
  3. customthe residue is chromatographed on silica gel using a 98

Sources & evidence

ORD record
ord-bac45866491f471989e6f3b764ca1cc4
Source dataset
uspto-grants-2006_05
Patent number
US07037935B2

Reaction notes

Loading…