Hydrochloric Acid → N-[3-(1-cyclohexyl-4-hydroxy-2-oxo-4a,5,6,7,8,8a-hexahydroquinolin-3-yl)-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazin-7-yl]methanesulfonamide

HRID 731362Notes

Reaction equation

HRID 731362 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[N:12]([CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)[C:13](=[O:32])[CH2:14][C:15]1[NH:20][C:19]2[CH:21]=[CH:22][C:23]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])=[CH:24][C:18]=2[S:17](=[O:31])(=[O:30])[N:16]=1)=O)C.[O-]CC.[Na+].Cl>C(O)C>[CH:33]1([N:12]2[CH:7]3[CH:6]([CH2:11][CH2:10][CH2:9][CH2:8]3)[C:4]([OH:3])=[C:14]([C:15]3[NH:20][C:19]4[CH:21]=[CH:22][C:23]([NH:25][S:26]([CH3:29])(=[O:27])=[O:28])=[CH:24][C:18]=4[S:17](=[O:31])(=[O:30])[N:16]=3)[C:13]2=[O:32])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 576712252-{Cyclohexyl-[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1lambda6-benzo[1,2,4]thiadiazin-3-yl)-acetyl]-amino}-cyclohexanecarboxylic acid ethyl ester

Product 1

HCID 135955791N-[3-(1-cyclohexyl-4-hydroxy-2-oxo-4a,5,6,7,8,8a-hexahydroquinolin-3-yl)-1,1-dioxo-4H-1$l^{6},2,4-benzothiadiazin-7-yl]methanesulfonamideYield 41.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
60 °C

Procedure

2-{Cyclohexyl-[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)-acetyl]-amino}-cyclohexanecarboxylic acid ethyl ester (0.48 g, 0.845 mmol) was dissolved in ethanol (15 mL), a 21% w/w solution of sodium ethoxide in ethanol (1.095 g, 3.38 mmol) was added. The mixture was stirred at 60° C. for 4 h and allowed to cool to 25° C. The mixture was poured into a 1.0 M aqueous hydrochloric acid solution (50 mL). The product started to precipitate and was collected by vacuum filtration. The precipitate was washed with water and dried under high vacuum to afford the pure product, N-[3-(1-cyclohexyl-4-hydroxy-2-oxo-1,2,4a,5,6,7,8,8a-octahydro-quinolin-3-yl)-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl]-methanesulfonamide (0.183 g, 0.35 mmol, 41.4%), as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ: 1.07-1.89 (18H, m), 2.32 (1H, bs), 3.05 (3H, s), 3.61-4.33 (3H, m), 7.47-7.60 (3H, m), 7.49-7.57 (3H, m), 10.15 (1H, s), 13.88 (1H, s). LC-MS (ESI) calcd for C23H30N4O6S2 522.16, found 523.4 [M+H+].

Workup

  1. temperatureto cool to 25° C
  2. customto precipitate
  3. filtrationwas collected by vacuum filtration
  4. washThe precipitate was washed with water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-2dadc4e37e0d4110b3ac15a93d4f4ccb
Source dataset
uspto-grants-2009_09
Patent number
US07582626B2

Reaction notes

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