Triethylamine → HCID 86686015, compound

HRID 2277720Notes

Reaction equation

HRID 2277720 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([C:12]1[CH:13]=[N:14][CH:15]=[C:16]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[CH:17]=1)[C:5]2([CH3:25])[CH3:24].[Cl:26][C:27]1[C:28]([C:33](O)=[O:34])=[N:29][CH:30]=[CH:31][CH:32]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([C:12]1[CH:13]=[N:14][CH:15]=[C:16]([N:18]3[CH2:23][CH2:22][N:21]([C:33]([C:28]4[C:27]([Cl:26])=[CH:32][CH:31]=[CH:30][N:29]=4)=[O:34])[CH2:20][CH2:19]3)[CH:17]=1)[C:5]2([CH3:25])[CH3:24]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8246323-Chloropyridine-2-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86686012HCID 86686012, compound

Product 1

HCID 86686015HCID 86686015, compoundYield 45.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-chloro-3,3-dimethyl-2-(5-piperazin-1-yl-pyridin-3-yl)-2,3-dihydro-isoindol-1-one (example 455 [C]) (52 mg, 0.146 mmol), 3-chloro-pyridine-2-carboxylic acid (25.3 mg, 0.161 mmol), HATU (83.3 mg, 0.219 mmol) and Et3N (29.5 mg, 0.292 mmol) in DCM (5 mL) was stirred for 2 hours at room temperature. The mixture was treated with water, and extracted with DCM. The organic layer was dried over anhy. Na2SO4 and after removal of solvent, the residue was purified by preparative HPLC to afford the title compound (33 mg, 45%) as a white solid. MS: 496.3 (M+H+).

Workup

  1. extractionextracted with DCM
  2. customThe organic layer was dried over anhy
  3. customNa2SO4 and after removal of solvent
  4. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-12f4882d4bf840209f944c390ae18522
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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