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 2408914Notes

Reaction equation

HRID 2408914 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
23 °C

Procedure

Ethanol (51 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, 1.4 M hydrochloric acid (0.961 ml, 1.345 mmol) was added to the reaction mixture, and the resulting mixture was then stirred for 26 minutes. Then, 1.4 M hydrochloric acid (0.641 ml, 0.897 mmol) was added to the reaction mixture over 4 minutes, and the resulting mixture was then stirred for 6 minutes. This operation was repeated further three times. Thereafter, 1.4 M hydrochloric acid (0.320 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 2° C. over 50 minutes. Two hours 30 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 (2.048 g, 4.246 mmol). Yield: 95%.

Workup

  1. stirringthe resulting mixture was then stirred for 26 minutes
  2. stirringthe resulting mixture was then stirred for 6 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 2° C. over 50 minutes
  6. filtrationTwo hours 30 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-60216dacf65d49299d1c4c5f1c7f8f5a
Source dataset
uspto-grants-2014_08
Patent number
US08815880B2

Reaction notes

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