(2-Thienylmethyl)amine → 2-chloro-6-methyl-N-(thiophen-2-ylmethyl)nicotinamide
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.[Cl:34][C:35]1[N:43]=[C:42]([CH3:44])[CH:41]=[CH:40][C:36]=1[C:37]([OH:39])=O.[S:45]1[CH:49]=[CH:48][CH:47]=[C:46]1[CH2:50][NH2:51]>CN(C=O)C.CC(=O)OCC.CCCCCC.CC(=O)OCC>[Cl:34][C:35]1[N:43]=[C:42]([CH3:44])[CH:41]=[CH:40][C:36]=1[C:37]([NH:51][CH2:50][C:46]1[S:45][CH:49]=[CH:48][CH:47]=1)=[O:39]Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
2.67 g (7.0 mmol) of HATU and 4.0 ml (23.2 mmol) of DIPEA were added at 0° C. to a solution of 1.0 g (5.8 mmol) of 2-chloro-6-methyl-nicotinic acid in DMF (20 ml), and the mixture was stirred for 20 min at 0° C. At that temperature, 656 mg (5.8 mmol) of thiophen-2-ylmethylamine were added. Stirring was then carried out for 16 h at RT. The mixture was then diluted with EA and washed in succession with sat. aq. NaHCO3 solution and brine. The organic phase was dried over Na2SO4, filtered and concentrated in vacuo. CC (hexane/EA 4:1) of the residue yielded 966 mg (3.6 mmol, 63%) of 2-chloro-6-methyl-N-(thiophen-2-ylmethyl)nicotinamide.
Workup
- stirringStirring
- waitwas then carried out for 16 h at RT
- washwashed in succession with sat. aq. NaHCO3 solution and brine
- dry with materialThe organic phase was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-576134ea9a1c469596421bcd43466380
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08084470B2
Reaction notes
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