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 2408902Notes

Reaction equation

HRID 2408902 reaction equation
Cl.C(O)C.[NH2:5][C:6]1[C:7]2[C:8]3[C:9](=[N:21][N:22]([CH2:24][C:25]4[C:30]([Cl:31])=[C:29]([O:32][CH3:33])[C:28]([CH3:34])=[CH:27][N:26]=4)[N:23]=2)[CH:10]=[C:11]([CH2:16][C:17]([NH:19][CH3:20])=[O:18])[C:12]=3[CH2:13][S:14][N:15]=1>O>[ClH:31].[NH2:5][C:6]1[C:7]2[C:8]3[C:9](=[N:21][N:22]([CH2:24][C:25]4[C:30]([Cl:31])=[C:29]([O:32][CH3:33])[C:28]([CH3:34])=[CH:27][N:26]=4)[N:23]=2)[CH:10]=[C:11]([CH2:16][C:17]([NH:19][CH3:20])=[O:18])[C:12]=3[CH2:13][S:14][N:15]=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%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3 M hydrochloric acid prepared by diluting 36.2% concentrated hydrochloric acid (1.75 kg, 17.4 mol) with water (4.5 L) was added dropwise to an ethanol (123 L) suspension of 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 (3.53 kg, 7.74 mol) at a temperature from 21° C. to 22° C. over 30 minutes, while the suspension was stirred. The resulting mixture was stirred for 4 hours. The obtained crystal was collected by filtration, was then washed with ethanol (17.6 L), and was then dried under reduced pressure at 40° C. for 17 hours, so as to obtain the above title compound (3.50 kg, 7.2 mol). Yield: 93%.

Workup

  1. stirringThe resulting mixture was stirred for 4 hours
  2. filtrationThe obtained crystal was collected by filtration
  3. washwas then washed with ethanol (17.6 L)
  4. customwas then dried under reduced pressure at 40° C. for 17 hours

Sources & evidence

ORD record
ord-8bd58353ab934a858ba636ad0086150a
Source dataset
uspto-grants-2014_08
Patent number
US08815880B2

Reaction notes

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