Triethylamine → N-((1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methyl)-5-chlorothiophene-2-carboxamide

HRID 643009

反応式

HRID 643009 の反応式
[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.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.[Br:44][C:45]1[CH:46]=[CH:47][C:48]([N:51]2[CH:55]=[C:54]([CH2:56][NH2:57])[N:53]=[CH:52]2)=[N:49][CH:50]=1>CN(C=O)C.CCOC(C)=O.O>[Br:44][C:45]1[CH:46]=[CH:47][C:48]([N:51]2[CH:55]=[C:54]([CH2:56][NH:57][C:7]([C:5]3[S:6][C:2]([Cl:1])=[CH:3][CH:4]=3)=[O:9])[N:53]=[CH:52]2)=[N:49][CH:50]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 950485-Chloro-2-thiophenecarboxylic acidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 68502878(1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methanamine

生成物 1

HCID 68507465N-((1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methyl)-5-chlorothiophene-2-carboxamide収率 21.4%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 5-chloro-2-thiophenecarboxylic acid (195 mg, 1.20 mmol) and triethylamine (0.400 mL, 2.87 mmol) in DMF (5 mL), BOP (550 mg, 1.24 mmol) was added. After 5 min of stirring, a solution of (1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methanamine (253 mg, 1.00 mmol) in DMF (5 mL) was added. The mixture was stirred at room temperature overnight. H2O and EtOAc were added. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, and concentrated in vacuo. The residue was purified by HPLC to give N-((1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methyl)-5-chlorothiophene-2-carboxamide (85 mg).

後処理

  1. stirringThe mixture was stirred at room temperature overnight
  2. customThe organic phase was separated
  3. washwashed with 5% NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by HPLC

出典と根拠

ORDレコード
ord-028b648dce5443338baad7827c4126f5
出典データセット
uspto-grants-2010_04
特許番号
US07696352B2

関連ノート

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