3,3-Dimethylbutylamine → 2-((5S)-2-(2-(4-tert-butylpiperazin-1-yl)-3,5-difluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetic acid

HRID 1695919

Reaktionsgleichung

Reaktionsgleichung von HRID 1695919
[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH2:4][NH2:5].[C:8]([N:12]1[CH2:17][CH2:16][N:15]([C:18]2[C:25]([F:26])=[CH:24][C:23]([F:27])=[CH:22][C:19]=2[CH:20]=O)[CH2:14][CH2:13]1)([CH3:11])([CH3:10])[CH3:9].[SH:28][C@@H:29]([CH2:33][C:34]([OH:36])=[O:35])[C:30](O)=[O:31]>C1(C)C=CC=CC=1>[C:8]([N:12]1[CH2:13][CH2:14][N:15]([C:18]2[C:25]([F:26])=[CH:24][C:23]([F:27])=[CH:22][C:19]=2[CH:20]2[N:5]([CH2:4][CH2:3][C:2]([CH3:7])([CH3:6])[CH3:1])[C:30](=[O:31])[C@H:29]([CH2:33][C:34]([OH:36])=[O:35])[S:28]2)[CH2:16][CH2:17]1)([CH3:11])([CH3:10])[CH3:9]

Komponenten

5

Edukt 3

HCID 197093,3-DimethylbutylamineHCID 3246154(s)-2-Mercaptosuccinic acidHCID 577743862-(4-Tert-butylpiperazin-1-yl)-3,5-difluorobenzaldehyde

Produkt 1

HCID 577744422-((5S)-2-(2-(4-tert-butylpiperazin-1-yl)-3,5-difluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetic acidAusbeute 27,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

3,3-Dimethylbutan-1-amine (0.7 g, 6.8 mmol) and 2-(4-tert-butylpiperazin-1-yl)-3,5-difluorobenzaldehyde (0.96 g, 3.4 mmol) were combined in toluene and heated to reflux overnight with a Dean-Stark trap attached. The reaction mixture was concentrated to a brown oil. This oil was redissolved in toluene and (S)-2-mercaptosuccinic acid (510 mg, 3.4 mmol) was added. The reaction mixture was heated at 80° C. for 16 hrs., concentrated to an oil, and triturated with ether to give a beige solid, which was filtered off and dried to give 2-((5S)-2-(2-(4-tert-butylpiperazin-1-yl)-3,5-difluorophenyl)-3-(3,3-dimethylbutyl)-4-oxothiazolidin-5-yl)acetic acid (0.45 g, 0.92 mmol, 27% yield) as a solid. LC/MS MH+ 498.45.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux overnight with a Dean-Stark trap
  3. concentrationThe reaction mixture was concentrated to a brown oil
  4. dissolutionThis oil was redissolved in toluene
  5. concentration, concentrated to an oil
  6. customtriturated with ether
  7. customto give a beige solid, which
  8. filtrationwas filtered off
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-34cb301596504420b4862507804db151
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163737B2

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