(R)-3-Pyrrolidinol → HCID 90042368, 화합물

HRID 1050234노트

반응식

HRID 1050234 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([OH:16])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[NH:17]1[CH2:21][CH2:20][C@@H:19]([OH:22])[CH2:18]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([N:17]3[CH2:21][CH2:20][C@@H:19]([OH:22])[CH2:18]3)=[O:16])=[CH:12][CH:13]=2)=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 2759337(R)-3-PyrrolidinolHCID 28183884-(4-Bromophenyl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

생성물 1

HCID 90042368HCID 90042368, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

4′-bromo-[1,1′-biphenyl]-4-carboxylic acid (2 g, 7.22 mmol), (R)-pyrrolidin-3-ol (1.3 g, 14.92 mmol), and HATU (5.5 g, 14.46 mmol) were dissolved in DMF (60 mL). To this solution was added TEA (4 ml, 28.7 mmol) and the reaction mixture was stirred under N2 at room temperature for 24 h. Then the volatiles were removed in vacuo and the resulting residue was partitioned between EtOAc and H2O. The organic layer was separated and washed with 1N HCl, saturated NaHCO3, and brine, and then dried over Na2SO4, filtered and concentrated in vacuo. Chromatography of the resulting residue over silica eluting with 3% MeOH in DCM afforded the desired product. LC-MS: calculated for C17H16BrNO2 345.04 observed m/e: 346.09 (M+H)+ (Rt: 1.62/4 min).

후처리

  1. customThen the volatiles were removed in vacuo
  2. customthe resulting residue was partitioned between EtOAc and H2O
  3. customThe organic layer was separated
  4. washwashed with 1N HCl, saturated NaHCO3, and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-d288cf4eb0f24f7a9a78fe96fb4471e9
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382243B2

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