2-Amino-4-[(methoxymethoxy)methyl]-3-thiophenesulfonamide → 1-[(Cyclopropylmethyl)amino]-4-hydroxy-3-{7-[(methoxymethoxy)methyl]-1,1-dioxido-4h-thieno[2,3-e][1,2,4]thiadiazin-3-yl}quinolin-2(1h)-one

HRID 552101Notes

Reaction equation

HRID 552101 reaction equation
CS[C:3](SC)=[C:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]([NH:15][CH2:16][CH:17]2[CH2:19][CH2:18]2)[C:5]1=[O:20].[NH2:23][C:24]1[S:25][CH:26]=[C:27]([CH2:33][O:34][CH2:35][O:36][CH3:37])[C:28]=1[S:29]([NH2:32])(=[O:31])=[O:30]>O1CCOCC1>[CH:17]1([CH2:16][NH:15][N:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:13]([OH:14])=[C:4]([C:3]3[NH:23][C:24]4[S:25][CH:26]=[C:27]([CH2:33][O:34][CH2:35][O:36][CH3:37])[C:28]=4[S:29](=[O:31])(=[O:30])[N:32]=3)[C:5]2=[O:20])[CH2:18][CH2:19]1

Participants

4

Reactant 2

HCID 574551872-Amino-4-[(methoxymethoxy)methyl]-3-thiophenesulfonamideHCID 670636773-[bis(methylthio)methylene]-1-[(cyclopropylmethyl)amino]quinoline-2,4(1H,3H)-dione

Product 1

HCID 1359745791-[(Cyclopropylmethyl)amino]-4-hydroxy-3-{7-[(methoxymethoxy)methyl]-1,1-dioxido-4h-thieno[2,3-e][1,2,4]thiadiazin-3-yl}quinolin-2(1h)-oneYield 52.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-[bis(methylthio)methylene]-1-[(cyclopropylmethyl)amino] quinoline-2,4(1H,3H)-dione (500.3, 1.5 mmol) and the product of 2-amino-4-[(methoxymethoxy)methyl]thiophene-3-sulfonamide (377.62 mg, 1.5 mmol) in dioxane (15 mL) was stirred at reflux for 1.5 hours and concentrated under reduced pressure. The residue was purified by chromatography on silica gel eluting with 0% to 10% ethyl acetate/dichloromethane to give 1-[(cyclopropylmethyl)amino]-4-hydroxy-3-{7-[(methoxymethoxy)methyl]-1,1-dioxido-4H-thieno[2,3-e][1,2,4]thiadiazin-3-yl}quinolin-2(1H)-one (384.7 mg, 52%). 1H NMR (300 MHz, DMSO-d6) δ 0.15 (m, 2 H) 0.42 (m, 2 H) 1.01 (m, 1 H) 2.84 (d, J=6.99 Hz, 2 H) 4.64 (s, 2 H) 4.71 (s, 2 H) 6.36 (br s, 1 H) 7.42 (m, 2 H) 7.86 (m, 1 H) 8.07 (d, J=8.46 Hz, 1 H) 8.16 (m, 1 H).

Workup

  1. temperatureat reflux for 1.5 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by chromatography on silica gel eluting with 0% to 10% ethyl acetate/dichloromethane

Sources & evidence

ORD record
ord-be1a9875775546c8afdced38fdcb58e3
Source dataset
uspto-grants-2011_05
Patent number
US07951800B2

Reaction notes

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