(1-chloro-6-methoxy-isoquinolin-3-yl)-(5-methyl-1H-pyrazol-3-yl)-amine → HCID 57799731, compound

HRID 2101187Notes

Reaction equation

HRID 2101187 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH:5]=[C:4]([NH:14][C:15]2[CH:19]=[C:18]([CH3:20])[NH:17][N:16]=2)[N:3]=1.[CH2:21]([Mg]Cl)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1COCC1.CN1C(=O)CCC1>[CH2:21]([C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[CH:5]=[C:4]([NH:14][C:15]2[CH:19]=[C:18]([CH3:20])[NH:17][N:16]=2)[N:3]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 57799674(1-chloro-6-methoxy-isoquinolin-3-yl)-(5-methyl-1H-pyrazol-3-yl)-amineHCID 178418336HCID 178418336, compound

Product 1

HCID 57799731HCID 57799731, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of (1-Chloro-6-methoxy-isoquinolin-3-yl)-(5-methyl-1H-pyrazol-3-yl)-amine (0.2543 g 1 equiv) in dry THF (2 ml) and NMP (0.2 ml) under Argon was added Fe(acac)3 (acac=acetylacetonate) (46.8 mg 0.15 equiv). The mixture was stirred for 10 min, and then Benzylmagnesium chloride (2M in THF, 0.792 ml 1.8 equiv) was added dropwise. The mixture was stirred at room temperature overnight. The product was purified by HPLC to give 11.5 mg of solid. LC-MS: m/e 345 (MH+).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customThe product was purified by HPLC

Sources & evidence

ORD record
ord-a8b4bb178ce94dbe8a24a43cdc6df209
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

Loading…