Acetic Acid → HCID 57799736, compound

HRID 2101048Notes

Reaction equation

HRID 2101048 reaction equation
[H-].[Na+].[C:3]1([SH:9])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[C:13]([NH:21][C:22]2[CH:26]=[C:25]([CH3:27])[NH:24][N:23]=2)[N:12]=1.C(O)(=O)C>COCCOC>[CH3:27][C:25]1[NH:24][N:23]=[C:22]([NH:21][C:13]2[N:12]=[C:11]([S:9][C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[C:20]3[C:15]([CH:14]=2)=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:26]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7969ThiophenolHCID 24758Sodium hydrideHCID 57799635(1-chloro-isoquinolin-3-yl)-(5-methyl-1H-pyrazol-3-yl)-amine

Product 1

HCID 57799736HCID 57799736, compoundYield 15.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

NaH (155 mg) was added to a solution of benzenethiol (500 mg) in DME (2 ml) and the mixture was stirred for 1 hour at room temperature. (1-chloro-isoquinolin-3-yl)-(5-methyl-1H-pyrazol-3-yl)-amine (100 mg) was then added, and the resulting mixture was heated at 150° C. for 30 minutes under microwave irradiation. The reaction mixture was acidified to pH=7 with acetic acid and purified by preparative LC-MS to give 20 mg of (5-methyl-1H-pyrazol-3-yl)-(1-phenylsulfanyl-isoquinolin-3-yl)-amine as a yellow solid. LC-MS: m/e 333(MH+).

Workup

  1. temperaturethe resulting mixture was heated at 150° C. for 30 minutes under microwave irradiation
  2. custompurified by preparative LC-MS

Sources & evidence

ORD record
ord-272dbc2cf9ad46a6bc1800623c3d282d
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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