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 2408909Notes

Reaction equation

HRID 2408909 reaction equation
O.[NH2:2][C:3]1[C:4]2[C:5]3[C:6](=[N:18][N:19]([CH2:21][C:22]4[C:27]([Cl:28])=[C:26]([O:29][CH3:30])[C:25]([CH3:31])=[CH:24][N:23]=4)[N:20]=2)[CH:7]=[C:8]([CH2:13][C:14]([NH:16][CH3:17])=[O:15])[C:9]=3[CH2:10][S:11][N:12]=1.Cl>C(O)C>[ClH:28].[NH2:2][C:3]1[C:4]2[C:5]3[C:6](=[N:18][N:19]([CH2:21][C:22]4[C:27]([Cl:28])=[C:26]([O:29][CH3:30])[C:25]([CH3:31])=[CH:24][N:23]=4)[N:20]=2)[CH:7]=[C:8]([CH2:13][C:14]([NH:16][CH3:17])=[O:15])[C:9]=3[CH2:10][S:11][N:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 962WaterHCID 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 186.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
25 °C

Procedure

Ethanol (36 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 25° C. Thereafter, concentrated hydrochloric acid (0.045 ml, 0.54 mmol) was added to the reaction mixture over 1 minute, and the resulting mixture was then stirred for 9 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. Then, ethanol (36 ml) was added thereto over 45 minutes, and 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 (2.020 g, 4.187 mmol). Yield: 93%.

Workup

  1. stirringthe resulting mixture was then stirred for 9 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-228b247c65d24ea4a7d288d6dc93d0cb
Source dataset
uspto-grants-2014_08
Patent number
US08815880B2

Reaction notes

Loading…