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Triethylamine → Methyl 4,4-difluoro-1-{[(4'-fluoro-4-methylbiphenyl-3-yl)acetyl]amino}cyclohexanecarboxylate

HRID 1466449
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Reaktionsgleichung

Reaktionsgleichung von HRID 1466449
Cl.[NH2:2][C:3]1([C:11]([O:13][CH3:14])=[O:12])[CH2:8][CH2:7][C:6]([F:10])([F:9])[CH2:5][CH2:4]1.C(N(CC)CC)C.[F:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[C:31]([CH2:36][C:37](O)=[O:38])[CH:30]=2)=[CH:25][CH:24]=1.P(Cl)(Cl)(Cl)=O>O1CCCC1>[F:9][C:6]1([F:10])[CH2:7][CH2:8][C:3]([NH:2][C:37](=[O:38])[CH2:36][C:31]2[CH:30]=[C:29]([C:26]3[CH:27]=[CH:28][C:23]([F:22])=[CH:24][CH:25]=3)[CH:34]=[CH:33][C:32]=2[CH3:35])([C:11]([O:13][CH3:14])=[O:12])[CH2:4][CH2:5]1
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Komponenten

6

Edukt 4

HCID 8471Triethylamine2×HCID 24813Phosphorus oxychlorideHCID 58545475(4'-Fluoro-4-methylbiphenyl-3-yl)acetic acidHCID 60196672Methyl 1-amino-4,4-difluorocyclohexanecarboxylate hydrochloride

Produkt 1

HCID 68283296Methyl 4,4-difluoro-1-{[(4'-fluoro-4-methylbiphenyl-3-yl)acetyl]amino}cyclohexanecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2.53 g (11 mmol) of the compound from Example 4A were initially charged in 50 ml of absolute tetrahydrofuran (THF). At 20° C., 3.07 ml of triethylamine were added dropwise, the mixture was stirred for 5 min and 2.44 g (10 mmol) of (4′-fluoro-4-methylbiphenyl-3-yl)acetic acid were added. After 15 min, a further 2.3 ml of triethylamine were added, followed immediately by the dropwise addition of 0.58 ml (6.2 mmol) of phosphorus oxychloride, and the mixture was stirred under reflux for 30 min. The mixture was concentrated under reduced pressure and the residue was purified by means of flash chromatography on silica gel using the mobile phase n-hexane/ethyl acetate 1:1. This gave 2.84 g (60% of theory) of the title compound of melting point 187° C.

Aufarbeitung

  1. waitAfter 15 min
  2. stirringthe mixture was stirred
  3. temperatureunder reflux for 30 min
  4. concentrationThe mixture was concentrated under reduced pressure
  5. customthe residue was purified by means of flash chromatography on silica gel using the mobile phase n-hexane/ethyl acetate 1:1

Quellen und Nachweise

ORD-Eintrag
ord-56c2e167e2c640c1bb1c952187a34a38
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09000026B2

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