Ethyl oxoacetate → HCID 86728306, compound

HRID 1776928Notes

Reaction equation

HRID 1776928 reaction equation
[F:1][C:2]1[C:3]2[CH:4]=[C:5]3[C:14]4[N:15]=[C:16]([C:19]5[C:20]([N:39]([CH3:44])[S:40]([CH3:43])(=[O:42])=[O:41])=[CH:21][C:22]6[O:26][C:25]([C:27]7[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=7)=[C:24]([C:34]([NH:36][CH3:37])=[O:35])[C:23]=6[CH:38]=5)[CH:17]=[CH:18][C:13]=4[O:12][CH2:11][N:6]3[C:7]=2[CH:8]=[CH:9][CH:10]=1.[C:45]([O:49][CH2:50][CH3:51])(=[O:48])[CH:46]=[O:47]>>[F:1][C:2]1[C:3]2[C:4]([CH:46]([OH:47])[C:45]([O:49][CH2:50][CH3:51])=[O:48])=[C:5]3[C:14]4[N:15]=[C:16]([C:19]5[C:20]([N:39]([CH3:44])[S:40]([CH3:43])(=[O:42])=[O:41])=[CH:21][C:22]6[O:26][C:25]([C:27]7[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=7)=[C:24]([C:34](=[O:35])[NH:36][CH3:37])[C:23]=6[CH:38]=5)[CH:17]=[CH:18][C:13]=4[O:12][CH2:11][N:6]3[C:7]=2[CH:8]=[CH:9][CH:10]=1

Participants

3

Reactant 2

HCID 70211Ethyl oxoacetateHCID 715091141426960-33-9

Product 1

HCID 86728306HCID 86728306, compound

Conditions

Temperature
115 °C

Procedure

A mixture of 5-(11-fluoro-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-2-yl)-2-(4-fluorophenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (500 mg, 0.814 mmol) and ethyl glyoxalate (323 μl, 1.627 mmol) was heated at 115° C. for 3 hours in a sealed tube. The reaction mixture was cooled to room temperature, concentrated under vacuum then applied onto 2-EP column (30 mm×250 mm) eluted with 30% IPA/CO2. This resulted in 108 mg (18.5%) of ethyl 2-(11-fluoro-2-(2-(4-fluorophenyl)-3-(methylcarbamoyl)-6-(N-methylmethylsulfonamido)benzofuran-5-yl)-6H-pyrido[2′,3′:5,6][1,3]oxazino[3,4-a]indol-12-yl)-2-hydroxyacetate (Compound 206) as a white solid. LC-MS (ES, m/z) C36H30F2N4O8S: 716. Found: 717 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under vacuum
  3. washeluted with 30% IPA/CO2

Sources & evidence

ORD record
ord-1d75c85d90c742f5bbc411ecac68433a
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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