Dimethylamine → HCID 66549234, Verbindung

HRID 2174386Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2174386
[Cl:1][C:2]1[CH:3]=[C:4]([C:10]2([C:28]([F:31])([F:30])[F:29])[O:14][N:13]=[C:12]([C:15]3[CH:20]=[CH:19][C:18]([N:21]4[CH2:24][CH:23]([C:25]([OH:27])=O)[CH2:22]4)=[CH:17][CH:16]=3)[CH2:11]2)[CH:5]=[C:6]([Cl:9])[C:7]=1[Cl:8].[CH3:32][N:33](C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)[CH3:34].F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.CNC>CN(C=O)C.C1COCC1>[CH3:32][N:33]([CH3:34])[C:25]([CH:23]1[CH2:24][N:21]([C:18]2[CH:17]=[CH:16][C:15]([C:12]3[CH2:11][C:10]([C:4]4[CH:3]=[C:2]([Cl:1])[C:7]([Cl:8])=[C:6]([Cl:9])[CH:5]=4)([C:28]([F:31])([F:29])[F:30])[O:14][N:13]=3)=[CH:20][CH:19]=2)[CH2:22]1)=[O:27]

Komponenten

7

Edukt 4

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86707796HCID 86707796, Verbindung

Produkt 1

HCID 66549234HCID 66549234, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a stirred solution of 1-{4-[5-(3,4,5-Trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-phenyl}-azetidine-3-carboxylic acid (Preparation 12, 0.1 g, 0.203 mmol) in DMF (3 mL) was added HATU (0.115 g, 0.304 mmol) HOBt (0.03 g, 0.223 mmol), DIPEA (0.052 g, 0.406 mmol) followed by addition of saturated solution of dimethyl amine in THF (2 mL) at 0° C. and stirred at 0° C. for 3 hours. After complete consumption of starting material, reaction mixture was quenched with water (20 mL), extracted with EtOAc (3×20 mL). Combined organic layer was washed with brine (50 mL), saturated solution of lithium chloride (50 mL), and water (50 mL), dried over sodium sulphate and evaporated in vacuo to get crude. Crude was purified by column chromatography on silica gel (100-200 mesh size). Compound was eluted using 0.6% methanol in DCM to afford white solid (0.050 g, 48%. 1H-NMR (400 MHz, CDCl3) δ: 2.94 (s, 3H), 2.97 (s, 3H), 3.61 (d, 1H, J=17.08 Hz), 3.69-3.77 (m, 1H), 4.02 (d, 1H, J=17.04 Hz), 4.11 (d, 4H, J=7.48 Hz), 6.40 (d, 2H, J=8.72 Hz), 7.46 (d, 2H, J=8.68 Hz), 7.63 (s, 2H); LC-MS (m/z): [M+H] 519.80.

Aufarbeitung

  1. customAfter complete consumption of starting material, reaction mixture
  2. customwas quenched with water (20 mL)
  3. extractionextracted with EtOAc (3×20 mL)
  4. washCombined organic layer was washed with brine (50 mL), saturated solution of lithium chloride (50 mL), and water (50 mL)
  5. dry with materialdried over sodium sulphate
  6. customevaporated in vacuo
  7. customto get crude
  8. customCrude was purified by column chromatography on silica gel (100-200 mesh size)
  9. washCompound was eluted
  10. customto afford white solid (0.050 g, 48%

Quellen und Nachweise

ORD-Eintrag
ord-879cebe0fe684bd2913cd2a78908c896
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09061013B2

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