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Methanol → 2-(4-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylic acid

HRID 1641060
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1641060
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([N:13]1[CH2:18][CH2:17][O:16][C:15]2[CH:19]=[CH:20][C:21]([C:23]3[S:24][C:25]([N:33]([CH3:43])[CH2:34][CH2:35][O:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)=[C:26]([C:28]([O:30]CC)=[O:29])[N:27]=3)=[CH:22][C:14]1=2)=[O:12].[OH-].[K+].CO>O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]([N:13]1[CH2:18][CH2:17][O:16][C:15]2[CH:19]=[CH:20][C:21]([C:23]3[S:24][C:25]([N:33]([CH3:43])[CH2:34][CH2:35][O:36][C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)=[C:26]([C:28]([OH:30])=[O:29])[N:27]=3)=[CH:22][C:14]1=2)=[O:12]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 59418665ethyl 2-(4-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylate

Produkt 1

HCID 468407892-(4-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylic acidAusbeute 8 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

The title compound 2-(4-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylic acid (20) was prepared by the following procedure: To ethyl 2-(4-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylate (20C) (0.210 g, 0.34 mmol) and KOH (0.1 g, 1.8 mmol) was added MeOH (2 mL) and water (5 mL). The reaction mixture was allowed to heat to 55° C. and stirred 24 hours. The reaction was monitored by LCMS. To the reaction mixture was added (0.1 g, 1.8 mmol). The reaction mixture was allowed to heat to 55° C. and stirred for 24 hours. The reaction mixture was cooled to rt and concentrated under reduced pressure. To the crude residue was added EtOAc and water. The layers were separated and extracted with EtOAc and the combined organic extracts were washed sequentially with water, brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The crude residue was purified by reverse phase HPLC to provide 0.015 g (8%) of the desired product 2-(4-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl) amino)thiazole-4-carboxylic acid (20): LC/MS (APCI): m/z 588.1 (M+H).

Aufarbeitung

  1. customThe title compound 2-(4-(benzo[d]thiazol-2-ylcarbamoyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)-5-(methyl(2-phenoxyethyl)amino)thiazole-4-carboxylic acid (20) was prepared by the following procedure
  2. additionTo the reaction mixture was added (0.1 g, 1.8 mmol)
  3. temperatureto heat to 55° C.
  4. stirringstirred for 24 hours
  5. temperatureThe reaction mixture was cooled to rt
  6. concentrationconcentrated under reduced pressure
  7. additionTo the crude residue was added EtOAc and water
  8. customThe layers were separated
  9. extractionextracted with EtOAc
  10. washthe combined organic extracts were washed sequentially with water, brine
  11. dry with materialdried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure
  14. customThe crude residue was purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-cab11f8704ca4e538abf30f6cd374a9f
Quelldatensatz
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08114893B2

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