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

HRID 643009

반응식

HRID 643009 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매2회HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-028b648dce5443338baad7827c4126f5
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07696352B2

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