1,2-Dichloroethane → HCID 75070613, compound

HRID 579652Notes

Reaction equation

HRID 579652 reaction equation
[CH:1]([C:4]1[N:9]=[C:8]([C:10]2[CH:19]=[C:18]([O:20][CH:21]3[CH2:38][CH:37]4[CH:23]([C:24](=[O:44])[N:25]([CH3:43])[CH2:26][CH2:27][CH2:28][CH2:29][CH:30]=[CH:31][CH:32]5[C:34]([C:40](O)=[O:41])([NH:35][C:36]4=[O:39])[CH2:33]5)[CH2:22]3)[C:17]3[C:12](=[C:13]([CH3:47])[C:14]([O:45][CH3:46])=[CH:15][CH:16]=3)[N:11]=2)[CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2].C(Cl)CCl.[CH:52]1([S:55]([NH2:58])(=[O:57])=[O:56])[CH2:54][CH2:53]1.C1CCN2C(=NCCC2)CC1>CN(C1C=CN=CC=1)C.CN(C=O)C.C(O)(=O)C>[CH:1]([C:4]1[N:9]=[C:8]([C:10]2[CH:19]=[C:18]([O:20][CH:21]3[CH2:38][CH:37]4[CH:23]([C:24](=[O:44])[N:25]([CH3:43])[CH2:26][CH2:27][CH2:28][CH2:29][CH:30]=[CH:31][CH:32]5[C:34]([C:40]([NH:58][S:55]([CH:52]6[CH2:54][CH2:53]6)(=[O:57])=[O:56])=[O:41])([NH:35][C:36]4=[O:39])[CH2:33]5)[CH2:22]3)[C:17]3[C:12](=[C:13]([CH3:47])[C:14]([O:45][CH3:46])=[CH:15][CH:16]=3)[N:11]=2)[CH:7]=[CH:6][CH:5]=1)([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 111,2-DichloroethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15765418CyclopropanesulfonamideHCID 66871229HCID 66871229, compound

Product 1

HCID 75070613HCID 75070613, compoundYield 39%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 17-[2-(6-isopropyl-2-pyridyl)-7-methoxy-8-methylquinolin-4-yloxy]-13-methyl-2,14-dioxo-3,13-diazatricyclo[13.3.0.04,6]octadec-7-ene-4-carboxylic acid (113, 200 mg, 0.31 mmol), DMAP (76.5 mg, 0.62 mmol), and EDC (151 mg, 0.78 mmol) in DMF (5 mL) was stirred at room temperature overnight (the activation of the acid was monitored by LC-MS). Then, cyclopropylsulfonamide (191 mg, 1.56 mmol) was added, followed by DBU (228 μL, 1.56 mmol). The resulting solution was stirred overnight at room temperature, then neutralized with acetic acid and evaporated. The residue was re-dissolved in MeOH and purified by preparative HPLC to give 90 mg (39%) of the title compound 114: m/z=744 (M+H)+.

Workup

  1. customevaporated
  2. dissolutionThe residue was re-dissolved in MeOH
  3. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-bc884c73b18441779c551f2bd21509ac
Source dataset
uspto-grants-2015_05
Patent number
US09040562B2

Reaction notes

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