Hydrochloric Acid → 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 hydrochloride

HRID 2408924Notes

Reaction equation

HRID 2408924 reaction equation
[NH2:1][C:2]1[C:3]2[C:4]3[C:5](=[N:17][N:18]([CH2:20][C:21]4[C:26]([Cl:27])=[C:25]([O:28][CH3:29])[C:24]([CH3:30])=[CH:23][N:22]=4)[N:19]=2)[CH:6]=[C:7]([CH2:12][C:13]([NH:15][CH3:16])=[O:14])[C:8]=3[CH2:9][S:10][N:11]=1.Cl>C(O)C>[ClH:27].[NH2:1][C:2]1[C:3]2[C:4]3[C:5](=[N:17][N:18]([CH2:20][C:21]4[C:26]([Cl:27])=[C:25]([O:28][CH3:29])[C:24]([CH3:30])=[CH:23][N:22]=4)[N:19]=2)[CH:6]=[C:7]([CH2:12][C:13]([NH:15][CH3:16])=[O:14])[C:8]=3[CH2:9][S:10][N:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid3×HCID 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 666180732-{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 hydrochlorideYield 188.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

Ethanol (72 ml) was added to 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 (2.068 g, 4.485 mmol), and the resulting mixture was then stirred at 20° C. Thereafter, 1 M hydrochloric acid (4.037 ml, 4.037 mmol) was added to the reaction mixture over 1 hour. Then, concentrated hydrochloric acid (0.111 ml, 1.332 mmol) was further added to the reaction mixture over 30 minutes, and the resulting mixture was then stirred for 30 minutes. Thereafter, concentrated hydrochloric acid (0.374 ml, 4.488 mmol) was added to the reaction mixture over 5 minutes, and the resulting mixture was then stirred for 1 hour. The reaction mixture was cooled to 4° C. over 46 minutes. Two hours later, the precipitated crystal was filtrated, was then washed with ethanol (10 ml), and was then dried under reduced pressure at 40° C. for 30 minutes, so as to obtain the above title compound (2.043 g, 4.235 mmol). Yield: 94%.

Workup

  1. stirringthe resulting mixture was then stirred for 30 minutes
  2. stirringthe resulting mixture was then stirred for 1 hour
  3. temperatureThe reaction mixture was cooled to 4° C. over 46 minutes
  4. filtrationTwo hours later, the precipitated crystal was filtrated
  5. washwas then washed with ethanol (10 ml)
  6. customwas then dried under reduced pressure at 40° C. for 30 minutes

Sources & evidence

ORD record
ord-d1a6208138e647b7986c4dbd2bfc32ad
Source dataset
uspto-grants-2014_08
Patent number
US08815880B2

Reaction notes

Loading…