HCID 11152684, compound → (1R)-1-(3,3-dimethylbutyl)-4-hydroxy-3-{7-[(methoxymethoxy)methyl]-1,1-dioxido-4H-thieno[2,3-e][1,2,4]thiadiazin-3-yl}-1-methylnaphthalen-2(1H)-one

HRID 494669Notes

Reaction equation

HRID 494669 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:11][O:12][CH2:13][O:14][CH3:15])[C:6]=1[S:7]([NH2:10])(=[O:9])=[O:8].CS[C:18](SC)=[C:19]1[C:28](=[O:29])[C@@:27]([CH2:31][CH2:32][C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:30])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]1=[O:37]>C1(C)C=CC=CC=1>[CH3:34][C:33]([CH3:36])([CH3:35])[CH2:32][CH2:31][C@:27]1([CH3:30])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]([OH:37])=[C:19]([C:18]2[NH:1][C:2]3[S:3][CH:4]=[C:5]([CH2:11][O:12][CH2:13][O:14][CH3:15])[C:6]=3[S:7](=[O:8])(=[O:9])[N:10]=2)[C:28]1=[O:29]

Participants

4

Reactant 2

HCID 11152684HCID 11152684, compoundHCID 574551872-Amino-4-[(methoxymethoxy)methyl]-3-thiophenesulfonamide

Product 1

HCID 135903311(1R)-1-(3,3-dimethylbutyl)-4-hydroxy-3-{7-[(methoxymethoxy)methyl]-1,1-dioxido-4H-thieno[2,3-e][1,2,4]thiadiazin-3-yl}-1-methylnaphthalen-2(1H)-oneYield 85%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of the product of Example 10E (2.02 g, 7.9 mmol) and the product of Example 49E (2.49 g, 6.9 mmol) in 200 mL of toluene was warmed to reflux for 5 h, cooled, and concentrated in vacuo. The crude material was chromatographed on silica gel with methanol/dichloromethane (1:99) to afford the title compound (3.03 g, 85% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.39 (td, J=12.59, 3.13 Hz, 1H) 0.72 (s, 9H) 0.82 (m, 1H) 1.57 (s, 3H) 2.04 (m, 1H) 2.22 (td, J=12.69, 4.41 Hz, 1H) 3.33 (s, 3H) 4.63 (s, 2H) 4.71 (s, 2H) 7.40 (s, 1H) 7.53 (m, 1H) 7.74 (d, J=4.04 Hz, 2H) 8.13 (d, J=7.72 Hz, 1H) 14.00 (s, 1H); MS (APCI−) m/z 517 (M−H)−; Analysis calc'd for (C25H30N2O6S2): C, 57.89; H, 5.83; N, 5.40. Found: C, 57.82; H, 6.12; N, 5.05.

Workup

  1. temperatureto reflux for 5 h
  2. temperaturecooled
  3. concentrationconcentrated in vacuo
  4. customThe crude material was chromatographed on silica gel with methanol/dichloromethane (1:99)

Sources & evidence

ORD record
ord-5c87e5a6b681487d8291ae7ce79ff34e
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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