Potassium Carbonate → 2-(pentylthio)-N-(2-thienylmethyl)-3-quinoline carboxamide

HRID 1949167Notes

Reaction equation

HRID 1949167 reaction equation
[SH:1][C:2]1[C:11]([C:12]([NH:14][CH2:15][C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C([O-])([O-])=O.[K+].[K+].I[CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>CN(C=O)C>[CH2:28]([S:1][C:2]1[C:11]([C:12]([NH:14][CH2:15][C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1)[CH2:29][CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123351-IodopentaneHCID 178523047HCID 178523047, compound

Product 1

HCID 469115432-(pentylthio)-N-(2-thienylmethyl)-3-quinoline carboxamideYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 300 mg (1.0 mmol) 2-mercapto-N-(thiophen-2-ylmethyl)quinoline-3-carboxamide (precursor VVV02) in DMF (2.3 ml) was mixed with 151 mg (1.1 mmol) K2CO3 at room temperature and stirred for 30 min. Then 131 μl (1.0 mmol) 1-iodopentane were added and the mixture was stirred for a further 3 days at RT. Then the mixture was concentrated to small volume under vacuum and the residue was taken up with EE and washed with water. The aqueous phase was extracted with EE and the combined organic phases were dried over MgSO4, filtered and concentrated to small volume under vacuum. Crystallisation of the residue from EE yielded 146 mg (0.4 mmol, 39%) 2-(pentylthio)-N-(2-thienylmethyl)-3-quinoline carboxamide. MS: m/z 371.1 [M+H]+.

Workup

  1. stirringthe mixture was stirred for a further 3 days at RT
  2. concentrationThen the mixture was concentrated to small volume under vacuum
  3. washwashed with water
  4. extractionThe aqueous phase was extracted with EE
  5. dry with materialthe combined organic phases were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to small volume under vacuum
  8. customCrystallisation of the residue from EE

Sources & evidence

ORD record
ord-937ccbab42934eb6976655d3caf35912
Source dataset
uspto-grants-2013_03
Patent number
US08399673B2

Reaction notes

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