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

HRID 1924898ノート

反応式

HRID 1924898 の反応式
[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]

参加物

6

反応物 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)

生成物 1

HCID 590231165-Amino-pyridine-2-carboxylic acid (2-diethylamino-ethyl)-amide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a61aeaa1337b41ada68f7fd24b6900f0
出典データセット
uspto-grants-2012_05
特許番号
US08178530B2

反応ノート

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