Trifluoroacetic acid → HCID 178443922, Verbindung

HRID 1727339

Reaktionsgleichung

Reaktionsgleichung von HRID 1727339
[CH2:1]([C@H:4]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])[C:5]([OH:7])=O)[CH2:2]C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CN1CCOCC1.[CH3:45][C:46]([NH2:57])=[N:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[C:51]([CH2:55][NH2:56])[CH:50]=1.Cl.Cl.C(O)(C(F)(F)F)=O>CN(C=O)C.CO>[C:46]([NH:47][CH2:48][C:49]1[CH:50]=[C:51]([CH:52]=[CH:53][CH:54]=1)[CH2:55][NH:56][C:5](=[O:7])[C@H:4]([CH2:1][CH3:2])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])(=[NH:57])[CH3:45]

Komponenten

8

Edukt 5

HCID 6422Trifluoroacetic acidHCID 79724-MethylmorpholineHCID 208925(R)-(-)-2-propyloctanoic acidHCID 27335151400w DihydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 178443922HCID 178443922, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

(R)-2-propyloctanoic acid (100 mg, 0.48 mmol) was dissolved in 1 mL DMF. HATU (201 mg, 0.53 mmol) and NMM (192 μL, 1.73 mmol) were added and the solution was stirred for 5 min. 1400-W (94 mg, 0.528 mmol) was added and the solution was stirred for 2 h at rt. The reaction was quenched with TFA (142 μL, 1.87 mmol) TFA and MeOH (1 mL) and purified by preparative HPLC (5% to 100%, ACN/water) to give the product (Example 6) as a white solid. 1H-NMR (500 MHz, DMSO-d6) δ 9.80 (s, 1H), 9.22 (s, 1H), 8.76 (s, 1H), 8.37 (t, 1H), 7.34-7.37 (m, 1H), 7.22-7.29 (m, 3H), 4.47 (d, 2H), 4.42 (d, 2H), 2.18-2.24 (m, 4H), 1.46-1.50 (m, 2H), 1.20-1.31 (m, 12H), 0.84-0.87 (m, 6H). MS (ESI) 346 (M+H).

Aufarbeitung

  1. stirringthe solution was stirred for 2 h at rt
  2. custompurified by preparative HPLC (5% to 100%, ACN/water)
  3. customto give the product (Example 6) as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-3ad9fb4353394988a2eef5df19168acc
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07495029B2

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