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 2408908Notes

Reaction equation

HRID 2408908 reaction equation
C(O)C.[NH2:4][C:5]1[C:6]2[C:7]3[C:8](=[N:20][N:21]([CH2:23][C:24]4[C:29]([Cl:30])=[C:28]([O:31][CH3:32])[C:27]([CH3:33])=[CH:26][N:25]=4)[N:22]=2)[CH:9]=[C:10]([CH2:15][C:16]([NH:18][CH3:19])=[O:17])[C:11]=3[CH2:12][S:13][N:14]=1.Cl>O>[ClH:30].[NH2:4][C:5]1[C:6]2[C:7]3[C:8](=[N:20][N:21]([CH2:23][C:24]4[C:29]([Cl:30])=[C:28]([O:31][CH3:32])[C:27]([CH3:33])=[CH:26][N:25]=4)[N:22]=2)[CH:9]=[C:10]([CH2:15][C:16]([NH:18][CH3:19])=[O:17])[C:11]=3[CH2:12][S:13][N:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 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 186.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
23 °C

Procedure

Ethanol (72 ml) and water (3.052 ml) were 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, concentrated hydrochloric acid (0.045 ml, 0.54 mmol) was added to the reaction mixture over 2 minutes, and the resulting mixture was then stirred for 10 minutes. This operation was repeated further nine times. Thereafter, the reaction mixture was stirred for 30 minutes, and concentrated hydrochloric acid (0.299 ml, 3.588 mmol) was added thereto. The resulting mixture was then stirred for 4 hours. 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 (2.022 g, 4.192 mmol). Yield: 94%.

Workup

  1. stirringthe resulting mixture was then stirred for 10 minutes
  2. stirringThereafter, the reaction mixture was stirred for 30 minutes
  3. stirringThe resulting mixture was then stirred for 4 hours
  4. filtrationThe 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-6c7abfe9fe52430cb5e375387964efcf
Source dataset
uspto-grants-2014_08
Patent number
US08815880B2

Reaction notes

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