Diisopropylethylamine → N-[(4-aminophenyl)methyl]pyridine-2-carboxamide

HRID 2234368

반응식

HRID 2234368 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([O-:9])=O.[NH2:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH2:16])=[CH:13][CH:12]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C>CN(C=O)C>[NH2:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15][NH:16][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[O:9])=[CH:13][CH:12]=1

참가 물질

6

반응물 4

HCID 81531DiisopropylethylamineHCID 4278144-AminobenzylamineHCID 6920223PicolinateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 60891447N-[(4-aminophenyl)methyl]pyridine-2-carboxamide수율 68.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Pyridine-2-carboxylate (Aldrich; 0.35 g, 2.84 mmol), 4-aminobenzylamine (Aldrich; 0.51 g, 4.26 mmol) and HATU (1.65 g, 4.26 mmol) were dissolved in DMF (7.5 ml). N,N-Diisopropylethylamine (1.5 ml, 8.53 mmol) was added and the mixture stirred at room temperature for 2 h. The mixture was absorbed on to an SCX column, washed with methanol and eluted with ammonia in methanol. Product containing fractions were concentrated and the residue purified by normal phase chromatography (2% MeOH/DCM) to give a yellow solid (440 mg). which was suspended in DCM/Et2O and filtered to give the title compound as a pale yellow solid (235 mg, 36%).

후처리

  1. customThe mixture was absorbed on to an SCX column
  2. washwashed with methanol
  3. washeluted with ammonia in methanol
  4. additionProduct containing fractions
  5. concentrationwere concentrated
  6. customthe residue purified by normal phase chromatography (2% MeOH/DCM)

출처 및 근거

ORD 기록
ord-5ced0b6da781499e8cfaad59ac1a9933
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709471B2

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