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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 552101
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HRID 552101 반응식
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
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참가 물질

4

반응물 2

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

생성물 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)-one수율 52.3%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-be1a9875775546c8afdced38fdcb58e3
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07951800B2

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