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 2408913Notes

Reaction equation

HRID 2408913 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 Acid4×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 191.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
23 °C

Procedure

Ethanol (41 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 23° C. Thereafter, 1.8 M hydrochloric acid (0.748 ml, 1.346 mmol) was added to the reaction mixture, and the resulting mixture was then stirred for 27 minutes. Then, 1.8 M hydrochloric acid (0.498 ml, 0.896 mmol) was added to the reaction mixture over 5 minutes, and the resulting mixture was then stirred for 5 minutes. This operation was repeated further three times. 1.8 M hydrochloric acid (0.249 ml, 0.448 mmol) was added to the reaction mixture, and the resulting mixture was then stirred for 30 minutes. Concentrated hydrochloric acid (0.299 ml, 3.588 mmol) was added to the reaction mixture, and the resulting mixture was then stirred for 1 hour. The reaction mixture was cooled to 3° C. over 50 minutes. Two hours 20 minutes 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 (2.070 g, 4.291 mmol). Yield: 96%.

Workup

  1. stirringthe resulting mixture was then stirred for 27 minutes
  2. stirringthe resulting mixture was then stirred for 5 minutes
  3. stirringthe resulting mixture was then stirred for 30 minutes
  4. stirringthe resulting mixture was then stirred for 1 hour
  5. temperatureThe reaction mixture was cooled to 3° C. over 50 minutes
  6. filtrationTwo hours 20 minutes later, the precipitated crystal was filtrated
  7. washwas then washed with ethanol (10 ml)
  8. customwas then dried under reduced pressure at 40° C. for 30 minutes

Sources & evidence

ORD record
ord-293e128c372c4ba3ab1b32ba32ed9655
Source dataset
uspto-grants-2014_08
Patent number
US08815880B2

Reaction notes

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