Triethylamine → 2,6-Diamino-N-(4-benzyloxy-benzyl)-nicotinamide

HRID 2080170

Reaction equation

HRID 2080170 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.[CH2:46]([O:53][C:54]1[CH:61]=[CH:60][C:57]([CH2:58][NH2:59])=[CH:56][CH:55]=1)[C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.N1C2C(=NC=CC=2)C=C1>CN(C)C=O.[Cl-].[Na+].O>[NH2:1][C:2]1[N:10]=[C:9]([NH2:11])[CH:8]=[CH:7][C:3]=1[C:4]([NH:59][CH2:58][C:57]1[CH:60]=[CH:61][C:54]([O:53][CH2:46][C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)=[CH:55][CH:56]=1)=[O:6]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 92264-AzaindoleHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 42928454-BenzyloxybenzylamineHCID 189772452,6-Diaminonicotinic acid

Product 1

HCID 114508922,6-Diamino-N-(4-benzyloxy-benzyl)-nicotinamideYield 27%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2,6-Diamino-nicotinic acid described in Preparation Example A-15 (0.6 g, 3.92 mmol), triethylamine (1.64 mL, 11.8 mmol) and benzotriazole-1-yloxy tris(dimethylamino)phosphonium hexafluorophosphate (2.6 g, 5.9 mmol) were dissolved in N,N-dimethylformamide (200 mL), 4-benzyloxy-benzylamine described in Preparation Example 1 (1.25 g, 5.9 mmol) was added thereto, and the solution was stirred at room temperature for 16 hours. After the reaction was completed, the reaction solution was poured into brine, and the solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, then concentrated, the obtained residue was purified by NH silica gel column chromatography (ethyl acetate:hexane=2:1, then ethyl acetate), the resulting solid was washed with solvent (chloroform:ethyl acetate=2:1), and the title compound (0.37 g, 1.1 mmol, 27%) was obtained.

Workup

  1. additionwas added
  2. extractionthe solution was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customthe obtained residue was purified by NH silica gel column chromatography (ethyl acetate
  6. washhexane=2:1, then ethyl acetate), the resulting solid was washed with solvent (chloroform:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-ba6d9f1c19c443cda9e49bab1bc9c6b3
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Linked notes

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