(2-Thienylmethyl)amine → HCID 68729573, compound

HRID 660063Notes

Reaction equation

HRID 660063 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[CH3:34][C:35]1[CH:36]=[N:37][C:38]([S:44][CH2:45][CH2:46][S:47]([C:50]2[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=2)(=[O:49])=[O:48])=[C:39]([CH:43]=1)[C:40]([OH:42])=O.[S:56]1[CH:60]=[CH:59][CH:58]=[C:57]1[CH2:61][NH2:62]>CN(C=O)C.CC(=O)OCC.CCCCCC.CC(=O)OCC>[C:50]1([S:47]([CH2:46][CH2:45][S:44][C:38]2[N:37]=[CH:36][C:35]([CH3:34])=[CH:43][C:39]=2[C:40]([NH:62][CH2:61][C:57]2[S:56][CH:60]=[CH:59][CH:58]=2)=[O:42])(=[O:49])=[O:48])[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1

Participants

8

Reactant 4

HCID 34005(2-Thienylmethyl)amineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68727942HCID 68727942, compound

Product 1

HCID 68729573HCID 68729573, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
0 °C

Procedure

456 mg (1.2 mmol) of HATU and 680 μl (4.0 mmol) of DIPEA were added at 0° C. to a solution of 337 mg (1.0 mmol) of 5-methyl-2-(2-(phenylsulfonyl)ethylthio)nicotinic acid in DMF (3 ml). After stirring for a further 15 min at 0° C., 113 mg (1.0 mmol) of thiophen-2-ylmethylamine were added and stirring was carried out for 16 hours at RT. The mixture was then diluted with EA and washed in succession with sat. aq. citric acid solution, saturated aqueous Na2CO3 solution and brine. The organic phase was dried over Na2SO4, filtered and concentrated in vacuo. CC (hexane/EA 7:3) of the residue yielded 418 mg (0.97 mmol, 97%) of 2-[2-(benzenesulfonyl)ethylthio]-5-methyl-N-(2-thienylmethyl)-nicotinamide. MS: m/z 433.1 [M+H]+

Workup

  1. stirringstirring
  2. waitwas carried out for 16 hours at RT
  3. washwashed in succession with sat. aq. citric acid solution, saturated aqueous Na2CO3 solution and brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1594452c34b34244a75279793938f880
Source dataset
uspto-grants-2011_12
Patent number
US08084470B2

Reaction notes

Loading…