Diethyl Ether → HCID 86652177, compound

HRID 2093558Notes

Reaction equation

HRID 2093558 reaction equation
C(OCC)C.[CH3:6][S:7]([OH:10])(=[O:9])=[O:8].[NH2:11][C:12]1[C:13]2[C:14]3[C:15](=[N:27][N:28]([CH2:30][C:31]4[C:36]([Cl:37])=[C:35]([O:38][CH3:39])[C:34]([CH3:40])=[CH:33][N:32]=4)[N:29]=2)[CH:16]=[C:17]([CH2:22][C:23]([NH:25][CH3:26])=[O:24])[C:18]=3[CH2:19][S:20][N:21]=1>C(#N)C>[CH3:6][S:7]([OH:10])(=[O:9])=[O:8].[NH2:11][C:12]1[C:13]2[C:14]3[C:15](=[N:27][N:28]([CH2:30][C:31]4[C:36]([Cl:37])=[C:35]([O:38][CH3:39])[C:34]([CH3:40])=[CH:33][N:32]=4)[N:29]=2)[CH:16]=[C:17]([CH2:22][C:23]([NH:25][CH3:26])=[O:24])[C:18]=3[CH2:19][S:20][N:21]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6395Methanesulfonic AcidHCID 666180742-{4-Amino-2-[(3-chloro-4-methoxy-5-methylpyridin-2-yl)methyl]-2,7-dihydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-8-yl}-N-methylacetamide

Product 1

HCID 86652177HCID 86652177, compoundYield 88.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
5 °C

Procedure

A diethyl ether solution (50 ml) of methanesulfonic acid (32 mg, 0.302 mmol) was added at 5° C. to an acetonitrile solution (150 ml) of 2-{4-amino-2-[(3-chloro-4-methoxy-5-methylpyridin-2-yl)methyl]-2,7-dihydro-6-thia-1,2,3,5-tetraazabenzo[cd]azulen-8-yl}-N-methylacetamide (151 mg, 0.339 mmol). The resulting mixture was stirred at 5° C. for 25 minutes. Thereafter, the solvent was distilled away under reduced pressure, an appropriate amount of diethyl ether was then added to the residue, and a solid was then collected by filtration. Thereafter, ethanol (1 ml) was added to the resulting solid, and the resulting mixture was then stirred at room temperature for approximately 1 day. Thereafter, a solid was collected by filtration, and it was then dried under reduced pressure at room temperature for 1 day, so as to obtain the title compound (145 mg, 0.268 mmol).

Workup

  1. distillationThereafter, the solvent was distilled away under reduced pressure
  2. additionan appropriate amount of diethyl ether was then added to the residue
  3. filtrationa solid was then collected by filtration
  4. additionThereafter, ethanol (1 ml) was added to the resulting solid
  5. stirringthe resulting mixture was then stirred at room temperature for approximately 1 day
  6. filtrationThereafter, a solid was collected by filtration, and it
  7. customwas then dried under reduced pressure at room temperature for 1 day

Sources & evidence

ORD record
ord-78ceabf0b5684ae6889c2be4d9218c89
Source dataset
uspto-grants-2013_05
Patent number
US08445504B2

Reaction notes

Loading…