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 2408923Notes

Reaction equation

HRID 2408923 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 187.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
30 °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 30° 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 6 minutes, and the resulting mixture was then stirred for 1 hour. The reaction mixture was cooled to 5° C. over 74 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 (2.031 g, 4.210 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 5° C. over 74 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-cfd34493d3de4f8fa803acd5b8e8f9ba
Source dataset
uspto-grants-2014_08
Patent number
US08815880B2

Reaction notes

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