1-Iodopentane → HCID 46911641, compound

HRID 1949170Notes

Reaction equation

HRID 1949170 reaction equation
[Na].CO[C:4](=O)[CH2:5][CH2:6][S:7][C:8]1[C:17]([C:18](=[O:26])[NH:19][CH2:20][C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:27]([F:30])([F:29])[F:28])[CH:14]=2)[N:9]=1.I[CH2:33][CH2:34]CCC>CO>[CH2:6]([S:7][C:8]1[C:17]([C:18]([NH:19][CH2:20][C:21]2[S:22][CH:23]=[CH:24][CH:25]=2)=[O:26])=[CH:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:27]([F:30])([F:29])[F:28])[CH:14]=2)[N:9]=1)[CH2:5][CH2:4][CH2:33][CH3:34]

Participants

5

Reactant 3

HCID 123351-IodopentaneHCID 5360545SodiumHCID 68512058HCID 68512058, compound

Product 1

HCID 46911641HCID 46911641, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

198 mg (8.6 mmol) sodium were added slowly to MeOH (86 ml) and the solution was stirred for 5 min at RT. Then a solution of 455 mg (1.0 mmol) 3-(3-(thiophen-2-ylmethylcarbamoyl)-6-(trifluoromethyl)quinolin-2-ylthio)propanoic acid methyl ester (Example 26) in MeOH (10 ml) was added at RT. The reaction solution was then heated for 30 min at 70° C. Then 396 μl (3.0 mmol) 1-iodopentane were added at RT and the mixture was stirred for 1 h at RT. Then the mixture was concentrated to small volume under vacuum and the residue was taken up with EE. It was washed with water and brine and the organic phase was dried over Na2SO4, filtered and concentrated to small volume under vacuum. 167 mg (0.4 mmol, 38%) 2-(pentylthio)-N-(2-thienylmethyl)-6-(trifluoromethyl)-3-quinoline carboxamide were obtained as residue. MS: m/z 439.1 [M+H]+.

Workup

  1. temperatureThe reaction solution was then heated for 30 min at 70° C
  2. stirringthe mixture was stirred for 1 h at RT
  3. concentrationThen the mixture was concentrated to small volume under vacuum
  4. washIt was washed with water and brine
  5. dry with materialthe organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to small volume under vacuum

Sources & evidence

ORD record
ord-96c43730cd114e3fa0c431a8aea5efd2
Source dataset
uspto-grants-2013_03
Patent number
US08399673B2

Reaction notes

Loading…