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 2408917Notes

Reaction equation

HRID 2408917 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 188.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
26 °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 26° 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 5 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 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 (2.042 g, 4.233 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 1 hour
  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-751f62acf1e14301b6bcfbe63c48ca38
Source dataset
uspto-grants-2014_08
Patent number
US08815880B2

Reaction notes

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