Biphenyl → (1,1'-Biphenyl)-2-carboxamide

HRID 1913347

반응식

HRID 1913347 반응식
[C:1]1([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[N:14]([C:16]([O:20]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN(C)C[C@@H](N)CC1SC=CC=1>CN(C=O)C.CCOC(C)=O>[C:1]1([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:6]([C:16]([NH2:14])=[O:20])=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

6

반응물 3

HCID 7095BiphenylHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58420129HCID 58420129, 화합물

생성물 1

HCID 83254(1,1'-Biphenyl)-2-carboxamide수율 45%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

Biphenyl acid 10 (40 mg, 0.064 mmol, 1 eq) and HBTU (49 mg, 0.13 mmol, 2 eq) were dissolved in DMF (1 mL) followed by the addition of (S)-N1,N1-dimethyl-3-(thiophen-2-yl)propane-1,2-diamine (23 mg, 0.13 mmol, 2 eq). The reaction mixture was stirred for 2 h, diluted with EtOAc and quenched with a saturated aqueous NaHCO3 solution. The reaction mixture was extracted with EtOAc (3×100 mL) and the combined organics were dried over MgSO4, filtered and concentrated in vacuo to afford an oil. The crude oil was purified by silica gel chromatography (2-5% MeOH/DCM, 0.1% Et3N) to afford 23 mg of biphenyl amide 251. Yield 45%.

후처리

  1. customquenched with a saturated aqueous NaHCO3 solution
  2. extractionThe reaction mixture was extracted with EtOAc (3×100 mL)
  3. dry with materialthe combined organics were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto afford an oil
  7. customThe crude oil was purified by silica gel chromatography (2-5% MeOH/DCM, 0.1% Et3N)

출처 및 근거

ORD 기록
ord-d46755a81dbc498894625f01696857a8
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08609706B2

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