Triethylamine → HCID 21963694, compound

HRID 2212205Notes

Reaction equation

HRID 2212205 reaction equation
[Cl:1][C:2]1[C:3]2[C:4]3[C:5](=[C:23]([CH3:26])[O:24][N:25]=3)[C:6](=[O:22])[N:7]([CH:12]3[CH2:17][CH2:16][CH2:15][N:14]([CH2:18][C:19]([OH:21])=O)[CH2:13]3)[C:8]=2[CH:9]=[CH:10][CH:11]=1.[NH2:27][C:28]1[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=1.Cl.CN(C)CCCN=C=NCC.ON1C2N=CC=CC=2N=N1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.CN(C)C=O>[Cl:1][C:2]1[C:3]2[C:4]3[C:5](=[C:23]([CH3:26])[O:24][N:25]=3)[C:6](=[O:22])[N:7]([CH:12]3[CH2:17][CH2:16][CH2:15][N:14]([CH2:18][C:19]([NH:27][C:28]4[CH:29]=[N:30][CH:31]=[CH:32][CH:33]=4)=[O:21])[CH2:13]3)[C:8]=2[CH:9]=[CH:10][CH:11]=1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 100093-AminopyridineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21963704HCID 21963704, compound

Product 1

HCID 21963694HCID 21963694, compoundYield 39.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a dry roundbottom flask add [3-(9-Chloro-3-methyl-4-oxo-5H-isoxazolo[4,3-c]quinolin-5-yl)-piperidin-1-yl]-acetic acid (50 mg, 0.11 mmol), 3-amino-pyridine (16 mg, 0.17 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (33 mg, 0.17 mmol), 1-hydroxy-7-azabenzotriazole (23 mg, 0.17 mmol), 4-dimethylamino-pyridine (2 mg, 0.01 mmol), and dimethylformamide (3 mL). Stir the reaction under nitrogen, and add triethylamine (30 μL, 0.22 mmol) dropwise. Stir the solution under nitrogen at room temperature overnight. Concentrate the mixture, partition between 20% isopropanol/chloroform and water, and separate. Wash the organic layer with saturated aqueous sodium bicarbonate solution, brine, dry over magnesium sulfate and concentrate. Purify by flash chromatography on silica gel (eluting with 0–0.5% methanol/chloroform) to give 19.8 mg of the title compound as an orange solid, 33% yield. 1H NMR: consistent with structure. MS (ion spray) 452 (M+).

Workup

  1. customthe reaction under nitrogen
  2. stirringStir the solution under nitrogen at room temperature overnight
  3. concentrationConcentrate the mixture
  4. custompartition between 20% isopropanol/chloroform and water
  5. customseparate
  6. washWash the organic layer with saturated aqueous sodium bicarbonate solution, brine
  7. dry with materialdry over magnesium sulfate
  8. concentrationconcentrate
  9. customPurify by flash chromatography on silica gel (eluting with 0–0.5% methanol/chloroform)

Sources & evidence

ORD record
ord-8332239913be476a92ac9175f0c70572
Source dataset
uspto-grants-2006_09
Patent number
US07101891B2

Reaction notes

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