Triethylamine → HCID 86686005, compound

HRID 2277714Notes

Reaction equation

HRID 2277714 reaction equation
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([N:9]2[C:17]([CH3:19])([CH3:18])[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([Cl:20])[CH:15]=3)[C:10]2=[O:21])[CH:6]=[N:7][CH:8]=1.CCN(CC)CC.[CH3:29][C:30]1[C:31]([C:36](O)=[O:37])=[N:32][CH:33]=[CH:34][CH:35]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C.CCOC(C)=O.O>[Cl:20][C:14]1[CH:15]=[C:16]2[C:11]([C:10](=[O:21])[N:9]([C:5]3[CH:4]=[C:3]([CH2:2][NH:1][C:36]([C:31]4[C:30]([CH3:29])=[CH:35][CH:34]=[CH:33][N:32]=4)=[O:37])[CH:8]=[N:7][CH:6]=3)[C:17]2([CH3:18])[CH3:19])=[CH:12][CH:13]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 2687573-Methylpicolinic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86686004HCID 86686004, compound

Product 1

HCID 86686005HCID 86686005, compoundYield 24%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To solution of 2-(5-aminomethyl-pyridin-3-yl)-5-chloro-3,3-dimethyl-2,3-dihydro-isoindol-1-one (30 mg, 0.1 mmol), Et3N (15.3 mg, 0.15 mmol) and 3-methyl-pyridine-2-carboxylic acid (13.7 mg, 0.1 mmol) in DMF (3 mL) was added HATU (57.0 mg, 0.15 mmol) at room temperature. The reaction mixture was stirred at room temperature for 1 hour. Both water and EtOAc were added and the organic layer was dried over anhy. Na2SO4, filtered and concentrated in vacuo to give a residue which was then purified by Prep HPLC to give the title compound (10 mg, 24%) as a solid. MS: 421.2 (M+H+).

Workup

  1. customthe organic layer was dried over anhy
  2. filtrationNa2SO4, filtered
  3. concentrationconcentrated in vacuo
  4. customto give a residue which
  5. customwas then purified by Prep HPLC

Sources & evidence

ORD record
ord-042015887ce44ed3bbad55f7787b9279
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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