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

HRID 2080170

反応式

HRID 2080170 の反応式
[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]

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ba6d9f1c19c443cda9e49bab1bc9c6b3
出典データセット
uspto-grants-2011_04
特許番号
US07932272B2

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