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 2408911Notes

Reaction equation

HRID 2408911 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 189.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
24 °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 24° C. Thereafter, 1 M hydrochloric acid (1.346 ml, 1.346 mmol) was added to the reaction mixture, and the resulting mixture was then stirred for 25 minutes. Then, 1 M hydrochloric acid (0.897 ml, 0.897 mmol) was added to the reaction mixture over 4 minutes, and the resulting mixture was then stirred for 7 minutes. This operation was repeated further twice. Thereafter, concentrated hydrochloric acid (0.037 ml, 0.444 mmol) was added to the reaction mixture over 1 minute, and the resulting mixture was then stirred for 9 minutes. This operation was repeated further twice, and the reaction mixture was then stirred for 30 minutes. Concentrated hydrochloric acid (0.374 ml, 4.488 mmol) was added to the reaction mixture, and the resulting mixture was then stirred for 1 hour. The reaction mixture was cooled to 10° C. over 1 hour. 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 (2.048 g, 4.246 mmol). Yield: 95%.

Workup

  1. stirringthe resulting mixture was then stirred for 25 minutes
  2. stirringthe resulting mixture was then stirred for 7 minutes
  3. stirringthe resulting mixture was then stirred for 9 minutes
  4. stirringthe reaction mixture was then stirred for 30 minutes
  5. stirringthe resulting mixture was then stirred for 1 hour
  6. temperatureThe reaction mixture was cooled to 10° C. over 1 hour
  7. filtrationTwo hours later, the precipitated crystal was filtrated
  8. washwas then washed with ethanol (10 ml)
  9. customwas then dried under reduced pressure at 40° C. for 30 minutes

Sources & evidence

ORD record
ord-bc62118d872140c3ac6ba81001918be2
Source dataset
uspto-grants-2014_08
Patent number
US08815880B2

Reaction notes

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