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

HRID 660047

반응식

HRID 660047 반응식
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]

참가 물질

8

반응물 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)

생성물 1

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

시약·촉매·용매 3

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매HCID 21226206Ethyl acetate hexane용매

반응 조건

온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-576134ea9a1c469596421bcd43466380
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084470B2

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