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 2408910Notes

Reaction equation

HRID 2408910 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 187.3%

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 three times. Concentrated hydrochloric acid (0.037 ml, 0.444 mmol) was added to the reaction mixture, 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 8 minutes, and the resulting mixture was then stirred for 1 hour 20 minutes. The reaction mixture was cooled to 8° 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 (2.026 g, 4.200 mmol). Yield: 94%.

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 30 minutes
  4. stirringthe resulting mixture was then stirred for 1 hour 20 minutes
  5. temperatureThe reaction mixture was cooled to 8° C. over 1 hour
  6. filtrationTwo hours 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-e528ae34451f4da6a36d97937df15f9c
Source dataset
uspto-grants-2014_08
Patent number
US08815880B2

Reaction notes

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