1-Hexanethiol → N-(6-Methylthioquinolin-5-yl)-2-(hexylthio)-decanoic amide

HRID 1440521Notes

Reaction equation

HRID 1440521 reaction equation
[CH3:1][S:2][C:3]1[C:4]([NH:13][C:14](=[O:25])[C@H:15](Br)[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2.[H-].[Na+].[CH2:28]([SH:34])[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>CN(C=O)C>[CH3:1][S:2][C:3]1[C:4]([NH:13][C:14](=[O:25])[CH:15]([S:34][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[CH:6]2

Participants

5

Reactant 3

HCID 81061-HexanethiolHCID 24758Sodium hydrideHCID 53825922(R)-N-(6-Methylthioquinolin-5-yl)-2-bromodecanoic amide

Product 1

HCID 3025722N-(6-Methylthioquinolin-5-yl)-2-(hexylthio)-decanoic amideYield 65.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

(R)-N-(6-Methylthioquinolin-5-yl)-2-bromodecanoic amide (43 mg, 0.10 mmol) in 1 ml of DMF was cooled to 0° C. To this was added a cooled suspension of NaH (9 mg, 0.38 mmol) and hexanethiol (67 mg, 0.57 mmol) in 1 ml DMF. The reaction was allowed to warm to rt over a period of 12 hours and quenched with 5 ml of saturated NH4Cl. The aqueous layer was extracted with ethyl acetate (3×10 ml). Purification of the organic phase by silica gel column chromatography (eluent: 100% CHCl3) yielded 30 mg (65% yield) of the desired product. 1H NMR (CDCl3) δ8.85 (1H, d, J=3 Hz), 8.62 (1H, s), 8.05 (3H, d, J=9 Hz), 8.00 (1H, d, J=9 Hz), 7.65 (1H, d, J=9 Hz), 7.40 (1H, dd, J=9, 9 Hz), 3.55 (1H, t, J=8 Hz), 2.80 (2H, t, J=8 Hz), 2.50 (3H, s), 2.20-1.30 (22H, m), 0.91 (6H, t, J=9 Hz).

Workup

  1. additionTo this was added
  2. customquenched with 5 ml of saturated NH4Cl
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×10 ml)
  4. customPurification of the organic phase by silica gel column chromatography (eluent: 100% CHCl3)

Sources & evidence

ORD record
ord-6c74ae3d143c4b0bbd9e78639566f69e
Source dataset
uspto-grants-1996_03
Patent number
US05498786

Reaction notes

Loading…