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3-[bis(methylthio)methylene]-1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)quinoline-2,4(1H,3H)-dione → 2-[4-hydroxy-3-{7-[(methoxymethoxy)methyl]-1,1-dioxido-4H-thieno[2,3-e][1,2,4]thiadiazin-3-yl}-2-oxoquinolin-1(2H)-yl]-1H-isoindole-1,3(2H)-dione

HRID 601330
Notes
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Reaction equation

HRID 601330 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]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]([N:30]2[C:38](=[O:39])[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31]2=[O:40])[C:20]1=[O:41]>C1(C)C=CC=CC=1>[OH:29][C:28]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]([N:30]2[C:31](=[O:40])[C:32]3[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:38]2=[O:39])[C:20](=[O:41])[C:19]=1[C:18]1[NH:1][C:2]2[S:3][CH:4]=[C:5]([CH2:11][O:12][CH2:13][O:14][CH3:15])[C:6]=2[S:7](=[O:8])(=[O:9])[N:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 103415063-[bis(methylthio)methylene]-1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)quinoline-2,4(1H,3H)-dioneHCID 574551872-Amino-4-[(methoxymethoxy)methyl]-3-thiophenesulfonamide

Product 1

HCID 1363584122-[4-hydroxy-3-{7-[(methoxymethoxy)methyl]-1,1-dioxido-4H-thieno[2,3-e][1,2,4]thiadiazin-3-yl}-2-oxoquinolin-1(2H)-yl]-1H-isoindole-1,3(2H)-dioneYield 61.5%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Procedure

The product of Example 309G (32.6 mg, 0.13 mmol) and the product of Example 350C (53 mg, 0.13 mmol) were reacted in toluene (3 mL) at 100° C. for 3 hours. The resulting precipitate was collected by filtration and washed with methanol and diethyl ether to give the title compound (45 mg, 61.5%). 1H NMR (300 MHz, DMSO-d6) δ 3.32 (s, 3 H), 4.61 (s, 2 H), 4.70 (s, 2 H), 7.28 (s, 1 H), 7.42 (m, 1 H), 7.70 (d, J=4.04 Hz, 2 H), 8.06 (m, 2 H), 8.11 (m, 2 H), 8.22 (d, J=8.09 Hz, 1 H). MS (ESI−) m/z 565 (M−H)−.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with methanol and diethyl ether

Sources & evidence

ORD record
ord-1a3e171b4f304a198d1bf144aa4ea1b7
Source dataset
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07902203B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes