Triethylamine → HCID 70654800, compound

HRID 2091570Notes

Reaction equation

HRID 2091570 reaction equation
[NH2:1][C@@H:2]([CH3:15])[CH2:3][NH:4][C:5]1[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][C:6]=1[C:7](O)=[O:8].CCN(CC)CC.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[Br:14][C:12]1[CH:11]=[CH:10][C:6]2[C:7](=[O:8])[NH:1][C@@H:2]([CH3:15])[CH2:3][NH:4][C:5]=2[CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 70654763HCID 70654763, compound

Product 1

HCID 70654800HCID 70654800, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the crude (S)-2-((2-aminopropyl)amino)-4-bromobenzoic acid (544 mg, 2.0 mmol) and Et3N (731 mg, 7.24 mmol) in DMF was added HATU (829 mg, 2.18 mmol). After 30 min, the reaction mixture was concentrated and purified by flash chromatography on silica gel (2-10% MeOH/DCM eluent) to provide (S)-8-bromo-3-methyl-3,4-dihydro-1H-benzo[e][1,4]diazepin-5(2H)-one as a white oily solid (464 mg, 91% yield). This material was dissolved in dioxane (20 mL), then treated with Pd2(dba)3 (83 mg, 0.09 mmol), PCy3 (121 mg, 0.43 mmol), diboron pinacol ester (595 mg, 2.35 mmol) and KOAc (532 mg, 5.43 mmol), then heated at 90° C. for 2 h. At completion, the reaction was cooled to room temperature, then filtered and concentrated. The crude material was flashed over silica gel (2-10% MeOH/DCM eluent) to provide (S)-3-methyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-1H-benzo[e][1,4]diazepin-5(2H)-one (527 mg, 96% yield) as a yellow solid.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. custompurified by flash chromatography on silica gel (2-10% MeOH/DCM eluent)

Sources & evidence

ORD record
ord-0f5a1956d0fa4736a2d57438d3c0815a
Source dataset
uspto-grants-2013_05
Patent number
US08440652B2

Reaction notes

Loading…