N,N-Diethylethylenediamine → 5-Amino-pyridine-2-carboxylic acid (2-diethylamino-ethyl)-amide

HRID 1366125노트

반응식

HRID 1366125 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.[CH2:11]([N:13]([CH2:17][CH3:18])[CH2:14][CH2:15][NH2:16])[CH3:12].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.CCN(C(C)C)C(C)C>C1COCC1>[CH2:11]([N:13]([CH2:17][CH3:18])[CH2:14][CH2:15][NH:16][C:8]([C:5]1[CH:4]=[CH:3][C:2]([NH2:1])=[CH:7][N:6]=1)=[O:10])[CH3:12]

참가 물질

6

반응물 4

HCID 60993N,N-DiethylethylenediamineHCID 81531DiisopropylethylamineHCID 41797265-Aminopyridine-2-carboxylic 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 590231165-Amino-pyridine-2-carboxylic acid (2-diethylamino-ethyl)-amide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

The 5-amino-pyridine-2-carboxylic acid is coupled to N,N-diethyl-ethane-1,2-diamine (0.47 mL, 3.32 mmol), in the presence of O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (1.26 g, 3.33 mmol), and DIPEA (0.59 mL, 3.33 mmol) in THF (10 mL). The mixture is stirred at room temperature for 48 hours. The solvent is removed in vacuo and the residue partitioned between water-EtOAc. The organic layer is dried over MgSO4, filtered and concentrated to give a residue purified by silica gel column chromatography. 5-Amino-pyridine-2-carboxylic acid (2-diethylamino-ethyl)-amide is isolated (394 mg, 100%) eluting with 96:4 DCM:NH3 (7M in MeOH).

후처리

  1. customThe solvent is removed in vacuo
  2. customthe residue partitioned between water-EtOAc
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a residue
  7. custompurified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-f783a01ec2e743d0874b10a7185f324b
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893058B2

반응 노트

불러오는 중…