Triethylamine → (9-(2-Fluoro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(5-isopropylthiophen-3-yl)methanone

HRID 1689379

Reaktionsgleichung

Reaktionsgleichung von HRID 1689379
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH:25]([C:28]1[S:32][CH:31]=[C:30]([C:33]([OH:35])=O)[CH:29]=1)([CH3:27])[CH3:26].[O:36]1[C:41]2([CH2:46][CH2:45][N:44]([CH2:47][C:48]3[C:49]([F:57])=[C:50]([CH2:54][CH2:55][OH:56])[CH:51]=[CH:52][CH:53]=3)[CH2:43][CH2:42]2)[CH2:40][NH:39][CH2:38][CH2:37]1.C(N(CC)CC)C>CN(C=O)C>[F:57][C:49]1[C:50]([CH2:54][CH2:55][OH:56])=[CH:51][CH:52]=[CH:53][C:48]=1[CH2:47][N:44]1[CH2:45][CH2:46][C:41]2([O:36][CH2:37][CH2:38][N:39]([C:33]([C:30]3[CH:29]=[C:28]([CH:25]([CH3:26])[CH3:27])[S:32][CH:31]=3)=[O:35])[CH2:40]2)[CH2:42][CH2:43]1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 35250805-Isopropylthiophene-3-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 579891872-(3-(1-Oxa-4,9-diazaspiro[5.5]undecan-9-ylmethyl)-2-fluorophenyl)ethanol

Produkt 1

HCID 57989041(9-(2-Fluoro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(5-isopropylthiophen-3-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

HATU (0.183 g) was added in one portion to a stirred solution at 0° C. of 5-isopropylthiophene-3-carboxylic acid (0.063 g) and 2-(3-(1-oxa-4,9-diazaspiro[5.5]undecan-9-ylmethyl)-2-fluorophenyl)ethanol (example 67, step f) (0.114 g) and triethylamine (0.155 mL) in DMF (5 mL). The reaction mixture was stirred at room temperature for 2 hours. The mixture was partitioned between ethyl acetate and brine, the organic layer was washed twice with brine, dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure. The crude product was purified by flash silica chromatography using 2.5% methanol in dichloromethane with 1% triethylamine as solvent. Pure fractions were evaporated to dryness to afford the subtitled compound. Yield 0.100 g.

Aufarbeitung

  1. customThe mixture was partitioned between ethyl acetate and brine
  2. washthe organic layer was washed twice with brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customthe solvent evaporated under reduced pressure
  6. customThe crude product was purified by flash silica chromatography
  7. customPure fractions were evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-8c82e9f442e8445a8f87877577cee025
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08148373B2

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