Acetic acid, azido-, ethyl ester → Ethyl 2-(5-(1-(5-acetamido-2',4'-difluoro-[1,1'-biphenyl]-3-yl)-1H-benzo[d]-imidazol-5-yl)-1H-1,2,3-triazol-1-yl)acetate

HRID 64192

반응식

HRID 64192 반응식
[C:1]([C:3]1[CH:29]=[CH:28][C:6]2[N:7]([C:10]3[CH:11]=[C:12]([NH:24][C:25](=[O:27])[CH3:26])[CH:13]=[C:14]([C:16]4[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=4[F:23])[CH:15]=3)[CH:8]=[N:9][C:5]=2[CH:4]=1)#[CH:2].[CH2:30]([O:32][C:33](=[O:38])[CH2:34][N:35]=[N+:36]=[N-:37])[CH3:31].O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>C(O)(C)(C)C.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[C:25]([NH:24][C:12]1[CH:11]=[C:10]([N:7]2[C:6]3[CH:28]=[CH:29][C:3]([C:1]4[N:35]([CH2:34][C:33]([O:32][CH2:30][CH3:31])=[O:38])[N:36]=[N:37][CH:2]=4)=[CH:4][C:5]=3[N:9]=[CH:8]2)[CH:15]=[C:14]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][C:17]=2[F:23])[CH:13]=1)(=[O:27])[CH3:26]

참가 물질

7

반응물 3

HCID 69480Acetic acid, azido-, ethyl esterHCID 23667548Sodium AscorbateHCID 89501250N-(5-(5-ethynyl-1H-benzo[d]imidazol-1-yl)-2',4'-difluorobiphenyl-3-yl)acetamide

생성물 1

HCID 117777692Ethyl 2-(5-(1-(5-acetamido-2',4'-difluoro-[1,1'-biphenyl]-3-yl)-1H-benzo[d]-imidazol-5-yl)-1H-1,2,3-triazol-1-yl)acetate수율 75%

시약·촉매·용매 3

HCID 24463Copper sulfate pentahydrate촉매HCID 962Water용매HCID 6386tert-Butanol용매

실험 절차

A mixture of N-(5-(5-ethynyl-1H-benzo[d]imidazol-1-yl)-2′,4′-difluorobiphenyl-3-yl)acetamide (258 mg, 0.6 mmol), ethyl-2-azidoacetate (180 mg, 0.8 mmol, 1.3 eq.), sodium ascorbate (125 mg, 0.6 mmol, 1.0 eq.) and copper sulfate pentahydrate (80 mg, 0.32 mmol, 0.5 eq.) in t-butanol and water (1:1, 3 ml) was stirred for 12 h at RT. The mixture was quenched with water and the precipitate formed was filtered and dried to give the product in 75% yield (250 mg).

후처리

  1. customThe mixture was quenched with water
  2. customthe precipitate formed
  3. filtrationwas filtered
  4. customdried
  5. customto give the product in 75% yield (250 mg)

출처 및 근거

ORD 기록
ord-69095af4fe5942e89ed7d2861e284c4f
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447091B2

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