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 2408922Notes

Reaction equation

HRID 2408922 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 191.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
24 °C

Procedure

Ethanol (36.7 L) 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 (1.07 kg, 2.28 mol), and the resulting mixture was then stirred at 24° C. Thereafter, 1 M hydrochloric acid (2.06 L, 2.06 mol) was added to the reaction mixture over 68 minutes. Then, concentrated hydrochloric acid (57 ml, 0.68 mol) was further added to the reaction mixture over 34 minutes, and the resulting mixture was then stirred for 30 minutes. Thereafter, concentrated hydrochloric acid (191 ml, 2.29 mol) was added to the reaction mixture over 9 minutes, and the resulting mixture was then stirred for 1 hour. The reaction mixture was cooled to 5° C. over 76 minutes. Twenty-two hours 30 minutes later, the precipitated crystal was filtrated, was then washed with ethanol (5 L), and was then dried under reduced pressure at 40° C. for 18 hours, so as to obtain the above title compound (1.05 kg, 2.18 mol). 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 76 minutes
  4. filtrationTwenty-two hours 30 minutes later, the precipitated crystal was filtrated
  5. washwas then washed with ethanol (5 L)
  6. customwas then dried under reduced pressure at 40° C. for 18 hours

Sources & evidence

ORD record
ord-07beba3a3c3c42308a6100b9a68f0eb3
Source dataset
uspto-grants-2014_08
Patent number
US08815880B2

Reaction notes

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