Hydrochloric Acid → HCID 118308082, Verbindung

HRID 1750461

Reaktionsgleichung

Reaktionsgleichung von HRID 1750461
[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=2[C:9]([OH:11])=O)[O:4][N:3]=1.[NH2:16][C@H:17]1[CH2:21][CH2:20][CH2:19][C@@H:18]1[NH:22]C(=O)OC(C)(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C.[ClH:61].O1CCOCC1>CN(C=O)C.CO>[ClH:61].[NH2:16][C@H:17]1[CH2:21][CH2:20][CH2:19][C@@H:18]1[NH:22][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=1[C:5]1[O:4][N:3]=[C:2]([CH3:1])[N:6]=1

Komponenten

9

Edukt 6

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 312751,4-DioxaneHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 17040218(1S,2S)-trans-N-Boc-1,2-cyclopentanediamineHCID 231463052-(3-Methyl-1,2,4-oxadiazol-5-yl)benzoic acid

Produkt 1

HCID 118308082HCID 118308082, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-(3-methyl-1,2,4-oxadiazol-5-yl)benzoic acid (CAS number 475105-77-2; 0.84 g, 4.12 mmol), tert-butyl N-[(1S,2S)-2-aminocyclopentyl]carbamate (CAS number 586961-34-4; 0.75 g, 3.74 mmol), HATU (2.14 g, 5.62 mmol) and triethylamine (1.57 ml, 11.23 mmol) was stirred in dry DMF (12.5 ml) at room temperature for 17 hours. The reaction mixture was partitioned between ethyl acetate and water, washed with water and brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude material was then purified by column chromatography (silica, 0-100% ethyl acetate/petrol). The resulting cream solid was recrystalised from ethyl acetate, to which was then added methanol (10 ml) and HCl in 1,4-dioxane (4M, 4.68 ml, 18.72 mmol) and the reaction was stirred at room temperature for 17 hours. The reaction was concentrated in vacuo and azeotropically distilled with toluene to afford the title compound.

Aufarbeitung

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washwashed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude material was then purified by column chromatography (silica, 0-100% ethyl acetate/petrol)
  7. customThe resulting cream solid was recrystalised from ethyl acetate, to which
  8. concentrationThe reaction was concentrated in vacuo
  9. distillationazeotropically distilled with toluene

Quellen und Nachweise

ORD-Eintrag
ord-6e020f263d164325bcfa26555829af99
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09156829B2

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