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 1444669Notes

Reaction equation

HRID 1444669 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-[(methoxy methoxy) 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, 2H) 0.42 (m, 2H) 1.01 (m, 1H) 2.84 (d, J=6.99 Hz, 2H) 4.64 (s, 2H) 4.71 (s, 2H) 6.36 (br s, 1H) 7.42 (m, 2H) 7.86 (m, 1H) 8.07 (d, J=8.46 Hz, 1H) 8.16 (m, 1H)

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-8c823a1ad03e4db7b100de10b0b442f5
Source dataset
uspto-grants-2010_02
Patent number
US07662958B2

Reaction notes

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