Hydrochloric Acid → HCID 67288444, compound

HRID 403654Notes

Reaction equation

HRID 403654 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:16][CH2:17][CH2:18][O:19][CH3:20])=[C:9]([NH:12]C(=O)C)[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:21]#[N:22].[Cl:23][C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][C:30]=1[O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=1)[NH2:27].CS(O)(=O)=O.Cl.C(=O)([O-])[O-].[K+].[K+]>CO.C(O)C>[NH2:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:16][CH2:17][CH2:18][O:19][CH3:20])[N:5]=[CH:4][C:3]([C:21]#[N:22])=[C:2]2[NH:27][C:26]1[CH:28]=[CH:29][C:30]([O:31][CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][N:34]=2)=[C:24]([Cl:23])[CH:25]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6395Methanesulfonic AcidHCID 11430Potassium CarbonateHCID 167812123-Chloro-4-(2-pyridylmethoxy)anilineHCID 67288333HCID 67288333, compound

Product 1

HCID 67288444HCID 67288444, compoundYield 68.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of N-(4-chloro-3-cyano-7-(2-methoxyethoxy)quinolin-6-yl)acetamide (6.3 g, 0.0197 mol, 1.00 equiv), 3-chloro-4-(2-pyridylmethoxy)aniline (4.7 g, 0.0201 mol, 1.00 equiv), methanesulfonic acid (0.7 ml, 0.0108 mol) and ethanol (150 ml) was stirred under refluxed for 6 hours and then 0.6N hydrogen chloride (300 ml, 0.18 mol) was added. The mixture was heated to 80° C. for 19 hours, and then cooled to 0° C. to form precipitate. The precipitated solids were filtered and then added to a solution of 1N potassium carbonate (100 ml, 0.1 mol) in methanol (150 ml) and then the mixture was stirred for 3 hours. The resulting mixture was filtered, washed with 1:1 methanol/water (300 ml) and dried to give product 6.4 g. MS (ESI) m/z: 475 (M+1).

Workup

  1. temperatureunder refluxed for 6 hours
  2. temperaturecooled to 0° C.
  3. customto form precipitate
  4. filtrationThe precipitated solids were filtered
  5. stirringthe mixture was stirred for 3 hours
  6. filtrationThe resulting mixture was filtered
  7. washwashed with 1:1 methanol/water (300 ml)
  8. customdried

Sources & evidence

ORD record
ord-553e33afbf5d4d988cca554616d4a325
Source dataset
uspto-grants-2014_06
Patent number
US08748453B2

Reaction notes

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