Chloroform → HCID 59340093, compound

HRID 905907Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[C:7](=[O:13])[C:6]([C:14]([NH:16][CH2:17][C:18]([O:20]CC)=[O:19])=[O:15])=[C:5]2[OH:23].C(Cl)(Cl)Cl.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[NH:62]1[CH2:67][CH2:66][O:65][CH2:64][CH2:63]1.CC(C)([O-])C.[Na+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:23][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([N:62]3[CH2:67][CH2:66][O:65][CH2:64][CH2:63]3)[CH:3]=2)[N:8]([CH3:12])[C:7](=[O:13])[C:6]=1[C:14]([NH:16][CH2:17][C:18]([OH:20])=[O:19])=[O:15]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of ethyl 2-(6-bromo-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate (202 mg, 527 μmol), Pd2dba3.CHCl3 (55 mg, 53 μmol), X-Phos (50 mg, 105 μmol) and morpholine (115 μl, 1318 μmol) in 1,4-dioxane (3 ml) was treated with sodium tert-butoxide (203 mg, 2109 μmol). The reaction was stirred at 80° C. in a sealed tube. After 21 hours, the solution was adsorped onto silica gel, concentrated in vacuo and purified by silica gel chromatography (eluant: 4% methanol/dichloromethane, followed by/dichloromethane+1% AcOH) and subsequently by RP HPLC (0-100% MeCN/water+1% TFA, 10 min) affording 21 mg (11%) of 2-(4-hydroxy-1-methyl-6-morpholino-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetic acid as an yellow solid.

Workup

concentrationconcentrated in vacuo
custompurified by silica gel chromatography (eluant: 4% methanol/dichloromethane, followed by/dichloromethane+1% AcOH) and subsequently by RP HPLC (0-100% MeCN/water+1% TFA, 10 min)

Sources & evidence

ORD record: ord-8f315524b9ad4478aab79171eae602ee
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012968B2

Reaction notes

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