Pyridine → HCID 67443505, compound

HRID 1800921Notes

Reaction equation

HRID 1800921 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]([C:16]1[CH:21]=[CH:20][CH:19]=C(NC)[CH:17]=1)[C:10]([CH3:25])([CH3:24])[CH2:9]2)=[O:5])[CH3:2].[N:26]1[CH:31]=CC=C[CH:27]=1.[CH3:32][N:33]([CH3:37])[C:34](Cl)=[O:35]>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[NH:12][CH:11]([C:16]1[CH:21]=[CH:20][CH:19]=[C:32]([N:33]([CH3:37])[C:34]([N:26]([CH3:31])[CH3:27])=[O:35])[CH:17]=1)[C:10]([CH3:24])([CH3:25])[CH2:9]2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6598Dimethylcarbamoyl ChlorideHCID 67443130HCID 67443130, compound

Product 1

HCID 67443505HCID 67443505, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of 3,3-dimethyl-2-(3-methylamino-phenyl)-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (338 mg, 1 mmol) in dichloromethane (5 mL) and pyridine (0.5 mL, 6 mmol) was added a solution of dimethylcarbamyl chloride (0.1 mL, 1.1 mmol) in dichloromethane (2 mL) dropwise at 0° C. The reaction mixture was stirred at 25° C. for 12 h. Then the reaction mixture was extracted with dichloromethane (2×50 mL), washed with water, dried over anhydrous sodium sulfate and concentrated in vacuo to afford 3,3-dimethyl-2-[3-(trimethyl-ureido)-phenyl]-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (409 mg, 100%) as a brown oil which was used for next step without further purification: LC/MS m/e calcd for C24H31N3O3 (M+H)+: 410.53, observed: 410.1.

Workup

  1. extractionThen the reaction mixture was extracted with dichloromethane (2×50 mL)
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8a09d09f8415495daf22442e4b2439aa
Source dataset
uspto-grants-2013_01
Patent number
US08344137B2

Reaction notes

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