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 2408920Notes

Reaction equation

HRID 2408920 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 190.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
26 °C

Procedure

Ethanol (180 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 (5.252 g, 11.21 mmol), and the resulting mixture was then stirred at 26° C. Thereafter, 1 M hydrochloric acid (10.09 ml, 10.09 mmol) was added to the reaction mixture over 1 hour. Then, concentrated hydrochloric acid (0.280 ml, 3.360 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 (0.934 ml, 11.21 mmol) was added to the reaction mixture over 7 minutes, and the resulting mixture was then stirred for 1 hour. The reaction mixture was cooled to 5° C. over 1 hour. Twenty hours later, the precipitated crystal was filtrated, was then washed with ethanol (25 ml), and was then dried under reduced pressure at 40° C. for 1 hour, so as to obtain the above title compound (5.145 g, 10.67 mmol). Yield: 95%.

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 1 hour
  4. filtrationTwenty hours later, the precipitated crystal was filtrated
  5. washwas then washed with ethanol (25 ml)
  6. customwas then dried under reduced pressure at 40° C. for 1 hour

Sources & evidence

ORD record
ord-f13f58047f714d03b8f28e6032118e10
Source dataset
uspto-grants-2014_08
Patent number
US08815880B2

Reaction notes

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