Triethylamine → HCID 69849213, compound

HRID 352257Notes

Reaction equation

HRID 352257 reaction equation
[Cl:1][C:2]1[C:3]2[C:4]3[C:5](=[C:21]([CH3:24])[O:22][N:23]=3)[C:6](=[O:20])[N:7]([C@H:12]3[CH2:17][CH2:16][CH2:15][C@@H:14]([N-]C)[CH2:13]3)[C:8]=2[CH:9]=[CH:10][CH:11]=1.Cl.[C:26](Cl)(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[N:29][CH:28]=1.[CH2:35]([N:37](CC)CC)C>ClCCl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[C:3]2[C:4]3[C:5](=[C:21]([CH3:24])[O:22][N:23]=3)[C:6](=[O:20])[N:7]([C@H:12]3[CH2:17][CH2:16][CH2:15][C@@H:14]([CH2:35][NH:37][C:26](=[O:33])[C:27]4[CH:32]=[CH:31][CH:30]=[N:29][CH:28]=4)[CH2:13]3)[C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 86588288HCID 86588288, compound

Product 1

HCID 69849213HCID 69849213, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (1R, 3S) 3-(9-chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-cyclohexyl methyl amide (700 mg, 2.0 mmol) in 35 mL of dichloromethane was added 440 mg (2.4 mmol) of nicotinoyl chloride hydrochloride, 0.85 mL (6.0 mmol) of triethylamine and 5 mg of 4-dimethylaminopyridine. The reaction mixture was stirred overnight at ambient temperature, then washed with 1 N hydrochloric acid. The aqueous layer was extracted with 20% isopropanol/chloroform. The combined organics were washed with saturated sodium carbonate, brine, dried over sodium sulfate, filtered and concentrated to dryness. The residue was chromatographed on silica gel using methanol/chloroform as eluent to yield 740 mg (82%) of the desired isomer as a white solid. MS (ion spray) 451.1 (M+1).

Workup

  1. washwashed with 1 N hydrochloric acid
  2. extractionThe aqueous layer was extracted with 20% isopropanol/chloroform
  3. washThe combined organics were washed with saturated sodium carbonate, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue was chromatographed on silica gel
  8. customto yield 740 mg (82%) of the desired isomer as a white solid

Sources & evidence

ORD record
ord-63fb10cddc204c77a784e7630c94042e
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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