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Hydrochloric Acid → N-[3-[1-(3,3-dimethylbutyl)-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 731295
Notes
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Reaction equation

HRID 731295 reaction equation
C(O[C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C@@H:7]1[N:12]([CH2:33][CH2:34][C:35]([CH3:38])([CH3:37])[CH3:36])[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:5])C.[O-]CC.[Na+].Cl>C(O)C.C(OCC)(=O)C>[CH3:37][C:35]([CH3:38])([CH3:36])[CH2:34][CH2:33][N:12]1[C:13](=[O:32])[C:14]([C:15]2[NH:20][C:19]3[CH:21]=[CH:22][C:23]([NH:25][S:26]([CH3:29])(=[O:27])=[O:28])=[CH:24][C:18]=3[S:17](=[O:31])(=[O:30])[N:16]=2)=[C:4]([OH:5])[CH:6]2[CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]2
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 69065399cis-2-{(3,3-Dimethylbutyl)-[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 135955949N-[3-[1-(3,3-dimethylbutyl)-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 35%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of cis-2-{(3,3-dimethylbutyl)-[2-(7-methanesulfonylamino-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-3-yl)acetyl]amino}-cyclohexanecarboxylic acid ethyl ester (138.7 mg, 0.243 mmol) in absolute ethanol (10 mL) was added a 21% w/w solution of sodium ethoxide in ethanol (0.91 mL, 2.44 mmol). After stirring at 60° C. for 13 h, the mixture was diluted with ethyl acetate and acidified with 1.0 M aqueous hydrochloric acid solution to pH 1. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (2×20 mL). The combined organic layers were dried over anhydrous magnesium sulfate and concentrated in vacuo. The crude mixture was purified by flash column chromatography (Teledyne Isco RediSep Flash Column; 0-100% ethyl acetate in hexanes) to afford the desired product, N-{3-[2-(3,3-dimethylbutyl)-5-hydroxy-3-oxo-2-aza-bicyclo[4.4.0]dec-4-en-4-yl]-1,1-dioxo-1,4-dihydro-1λ6-benzo[1,2,4]thiadiazin-7-yl}-methanesulfonamide (44.3 mg, 0.084 mmol, 35%), as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ 0.94 (9H, s), 1.10-1.87 (9H, m), 2.32 (1H, bs), 3.04 (3H, s), 2.92-3.82 (4H, m), 7.47-7.58 (3H, m), 10.13 (1H, bs). LC-MS (ESI) calcd for C23H32N4O6S2 524.18, found 525.3 [M+H+]. Anal. calcd for C23H32N4O6S2: C, 52.65; H, 6.15; N, 10.68; S, 12.22, found C, 52.56; H, 6.10; N, 10.71; S, 12.16.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×20 mL)
  3. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude mixture was purified by flash column chromatography (Teledyne Isco RediSep Flash Column; 0-100% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-979882098deb4fb3a3f50d1cb8b34f5e
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07582626B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes