Ammonium Chloride → HCID 59429706, compound

HRID 1968717Notes

Reaction equation

HRID 1968717 reaction equation
[Cl:1][C:2]1[C:3]([CH2:16][C:17]([NH2:19])=[O:18])=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([CH2:12][N:13]([CH3:15])[CH3:14])=[CH:5]2.C[O:21][C:22](=O)[C:23]([C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:27][CH:26]=1)=O.CC([O-])(C)C.[K+].[NH4+].[Cl-]>C1COCC1>[Cl:1][C:2]1[C:3]([C:16]2[C:17](=[O:18])[NH:19][C:22](=[O:21])[C:23]=2[C:25]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[NH:27][CH:26]=2)=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([CH2:12][N:13]([CH3:14])[CH3:15])=[CH:5]2

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 588944Methyl 3-indoleglyoxylateHCID 23665647Potassium tert-butoxideHCID 66882216HCID 66882216, compound

Product 1

HCID 59429706HCID 59429706, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(6-chloro-3-dimethylaminomethyl-quinolin-5-yl)-acetamide (100 mg, 0.36 mmol) and (1H-indol-3-yl)-oxo-acetic acid methyl ester (110 mg, 0.54 mmol) in anhydrous THF was added dropwise a 1 M solution of t-BuOK in THF (1.8 mL) under an argon atmosphere at 0° C. The resulting deep red reaction mixture was stirred for 30 min. at 0° C., poured into a saturated aqueous NH4Cl solution and extracted twice with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated at reduced pressure to afford an orange solid. Purification by size exclusion chromatography (Sephadex LH-20, MeOH afforded the title compound as an orange solid (88.3 mg, 0.205 mmol, 57%). 1H NMR (400 MHz, DMSO-d6, 298 K): δ=11.88 (bs, 1H), 11.25 (bs, 1H), 8.69 (d, J=1.9 Hz, 1H), 8.10 (d, J=9.0 Hz, 1H), 8.02 (s, 1H), 7.91 (d, J=9.0 Hz, 1H), 7.85 (bs, 1H), 7.26 (d, J=8.1 Hz, 1H), 6.88 (t, J=7.4 Hz, 1H), 6.44 (t, J=7.4 Hz, 1H), 6.12 (d, J=8.1 Hz, 1H), 3.36 (AB-system: δA=3.48 (d, JAB=−13.2 Hz, 1H), δB=3.25 (d, JAB=−13.2 Hz, 1H)), 1.78 (s, 6H). MS (ES+): 431 (M(C24H1935ClN4O2)+H)+.

Workup

  1. customThe resulting deep red reaction mixture
  2. extractionextracted twice with EtOAc
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated at reduced pressure
  7. customto afford an orange solid
  8. customPurification by size exclusion chromatography (Sephadex LH-20, MeOH

Sources & evidence

ORD record
ord-a19147c8a11240648b27d9b9995d2fa3
Source dataset
uspto-grants-2013_04
Patent number
US08426440B2

Reaction notes

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