Triethylamine → 2-Amino-N-(5-bromo-benzofuran-2-ylmethyl)-6-methoxymethyl-nicotinamide

HRID 1171231ノート

反応式

HRID 1171231 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([CH2:10][NH2:11])=[CH:7][C:6]=2[CH:12]=1.[NH2:13][C:14]1[N:22]=[C:21]([CH2:23][O:24][CH3:25])[CH:20]=[CH:19][C:15]=1[C:16](O)=[O:17].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>O.CN(C)C=O>[NH2:13][C:14]1[N:22]=[C:21]([CH2:23][O:24][CH3:25])[CH:20]=[CH:19][C:15]=1[C:16]([NH:11][CH2:10][C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:12][C:6]=2[CH:7]=1)=[O:17]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 2795538(5-Bromobenzo[b]furan-2-yl)methylamineHCID 231304372-Amino-6-methoxymethylnicotinic acid

生成物 1

HCID 576082252-Amino-N-(5-bromo-benzofuran-2-ylmethyl)-6-methoxymethyl-nicotinamide収率 40.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To an N,N-dimethylformamide (10 mL) solution of C-(5-bromo-benzofuran-2-yl)-methylamine (455 mg, 2.01 mmol) described in Production Example 56-1-4 were added 2-amino-6-methoxymethyl-nicotinic acid (293 mg, 1.61 mmol) described in Production Example 4-1-5, triethylamine (700 μL, 5.03 mmol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (1.07 g, 2.41 mmol) at room temperature, which was stirred for 12 hours. Water was added to the reaction solution at room temperature followed by extraction with ethyl acetate. The organic layer was washed with water and sat. NaCl followed by drying over anhydrous magnesium sulfate, filtering and concentrating the filtrate under a reduced pressure. The residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=1:1) to obtain the title compound (255 mg, 33%) as a white solid.

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and sat. NaCl
  3. dry with materialby drying over anhydrous magnesium sulfate
  4. filtrationfiltering
  5. concentrationconcentrating the filtrate under a reduced pressure
  6. customThe residue was purified by NH silica gel column chromatography (heptane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-d8269bad9286466ebde3c8c72d0386d1
出典データセット
uspto-grants-2010_11
特許番号
US07829585B2

反応ノート

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