Isoamylamine → 2-[[3,3-difluoro-3-(4-fluorophenyl)-propyl]-sulfanyl]-N-(3-methyl-butyl)-pyridine-3-carboxylic acid amide

HRID 1925558Notes

Reaction equation

CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:34][C:35]([F:55])([C:48]1[CH:53]=[CH:52][C:51]([F:54])=[CH:50][CH:49]=1)[CH2:36][CH2:37][S:38][C:39]1[N:47]=[CH:46][CH:45]=[CH:44][C:40]=1[C:41]([OH:43])=O.[CH3:56][CH:57]([CH3:61])[CH2:58][CH2:59][NH2:60]>C(Cl)Cl.CC(=O)OCC.CCCCCC>[F:55][C:35]([F:34])([C:48]1[CH:53]=[CH:52][C:51]([F:54])=[CH:50][CH:49]=1)[CH2:36][CH2:37][S:38][C:39]1[C:40]([C:41]([NH:60][CH2:59][CH2:58][CH:57]([CH3:61])[CH3:56])=[O:43])=[CH:44][CH:45]=[CH:46][N:47]=1

Participants

Conditions

Temperature: 0 °C

Procedure

320 μl (1.83 mmol) of DIPEA and 350 mg (0.91 mmol) of HATU were added at 0° C. to a solution of 150 mg (0.46 mmol) of 2-(3,3-difluoro-3-(4-fluorophenyl)propylthio)-nicotinic acid in DCM (10 ml). After stirring for 30 min at 0° C., 63 μl (0.55 mmol) of 3-methylbutan-1-amine were added and then the mixture was stirred for 16 h at RT. Dilution with water (20 ml) and extraction with DCM (2×20 ml) were then carried out. The combined organic phases were washed with water and brine, dried over Na2SO4, filtered and concentrated in vacuo. CC (EA/hexane 7:3) of the residue yielded 100 mg (0.25 mmol, 55%) of 2-[[3,3-difluoro-3-(4-fluorophenyl)-propyl]-sulfanyl]-N-(3-methyl-butyl)-pyridine-3-carboxylic acid amide. MS: m/z 397.1 [m+H]+.

Workup

stirringthe mixture was stirred for 16 h at RT
extractionDilution with water (20 ml) and extraction with DCM (2×20 ml)
washThe combined organic phases were washed with water and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-881e027f58c043c8a96d145817bc6702
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08178684B2

Reaction notes

Loading…