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

HRID 1050234Notes

Reaction equation

HRID 1050234 reaction equation
[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

Participants

5

Reactant 3

HCID 2759337(R)-3-PyrrolidinolHCID 28183884'-Bromo[1,1'-biphenyl]-4-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 90042368HCID 90042368, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d288cf4eb0f24f7a9a78fe96fb4471e9
Source dataset
uspto-grants-2016_07
Patent number
US09382243B2

Reaction notes

Loading…