Dimethylamine → (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(6-(dimethylamino)nicotinoyloxy)acetoxy)-ethyl)pyridine 1-oxide

HRID 1776651Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1776651
[Cl:1][C:2]1[CH:3]=[N+:4]([O-:40])[CH:5]=[C:6]([Cl:39])[C:7]=1[CH2:8][C@H:9]([O:25][C:26](=[O:38])[CH2:27][O:28][C:29](=[O:37])[C:30]1[CH:35]=[CH:34][C:33](Cl)=[N:32][CH:31]=1)[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH:17]([F:19])[F:18])=[C:12]([O:20][CH2:21][CH:22]2[CH2:24][CH2:23]2)[CH:11]=1.[CH3:41][NH:42][CH3:43]>C1COCC1>[Cl:1][C:2]1[CH:3]=[N+:4]([O-:40])[CH:5]=[C:6]([Cl:39])[C:7]=1[CH2:8][C@@H:9]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH:17]([F:18])[F:19])=[C:12]([O:20][CH2:21][CH:22]2[CH2:24][CH2:23]2)[CH:11]=1)[O:25][C:26](=[O:38])[CH2:27][O:28][C:29](=[O:37])[C:30]1[CH:35]=[CH:34][C:33]([N:42]([CH3:43])[CH3:41])=[N:32][CH:31]=1

Komponenten

4

Edukt 2

HCID 674DimethylamineHCID 86679594(S)-3,5-dichloro-4-(2-(2-(6-chloronicotinoyloxy)acetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)pyridine 1-oxide

Produkt 1

HCID 86679595(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(6-(dimethylamino)nicotinoyloxy)acetoxy)-ethyl)pyridine 1-oxideAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of (S)-3,5-dichloro-4-(2-(2-(6-chloronicotinoyloxy)acetoxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)pyridine 1-oxide (202 mg, 0.327 mmol) and dimethylamine (327 μl, 0.654 mmol) in dry THF (5 ml) was stirred at room temperature for 2 days. The solvent was evaporated and the residue was portioned between sat. sol. NaHCO3 and ethyl acetate; the organic phase was washed with brine, dried over Na2SO4, filtered and evaporated and the residue was triturated with iPr2O, filtered and dried under vacuum to give (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-(2-(6-(dimethylamino)nicotinoyloxy)acetoxy)-ethyl)pyridine 1-oxide as a white solid (180 mg, 0.287 mmol, 88% yield, LC-MS purity (BPI): 98%, MS/ESI+ 626.24 [MH]+, [αD]=−37.04, c=0.50, DCM).

Aufarbeitung

  1. customThe solvent was evaporated
  2. washthe organic phase was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customthe residue was triturated with iPr2O
  7. filtrationfiltered
  8. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f4ab5715ca774dcf8148efa0d1f7d97e
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09265768B2

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