(2-Thienylmethyl)amine → 2-chloro-6-methyl-N-(thiophen-2-ylmethyl)nicotinamide

HRID 660047

反応式

HRID 660047 の反応式
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]

参加物

8

反応物 4

HCID 34005(2-Thienylmethyl)amineHCID 81531DiisopropylethylamineHCID 1217242-Chloro-6-methylnicotinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

生成物 1

HCID 866288362-chloro-6-methyl-N-(thiophen-2-ylmethyl)nicotinamide収率 63%

試薬・触媒・溶媒 3

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  1. stirringStirring
  2. waitwas then carried out for 16 h at RT
  3. washwashed in succession with sat. aq. NaHCO3 solution and brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-576134ea9a1c469596421bcd43466380
出典データセット
uspto-grants-2011_12
特許番号
US08084470B2

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