Dimethylformamide → HCID 67305476, Verbindung

HRID 535114Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 535114
[C:1]([O:5][C:6]([C@H:8]1[CH2:13][C:12]([F:15])([F:14])[CH2:11][NH:10][C@@H:9]1[C:16]([OH:18])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:20][C:21]1[CH:28]=[C:27]([C:29]2[CH2:30][CH2:31][NH:32][CH2:33][CH:34]=2)[CH:26]=[C:25]([CH3:35])[C:22]=1[C:23]#[N:24].CN(C)C=O.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(CC)C(C)C)(C)C>>[C:23]([C:22]1[C:25]([CH3:35])=[CH:26][C:27]([C:29]2[CH2:34][CH2:33][N:32]([C:16]([C@@H:9]3[C@@H:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][C:12]([F:14])([F:15])[CH2:11][NH:10]3)=[O:18])[CH2:31][CH:30]=2)=[CH:28][C:21]=1[CH3:20])#[N:24]

Komponenten

6

Edukt 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67304512(2S,3S)-3-(tert-butoxycarbonyl)-5,5-difluoropiperidine-2-carboxylic AcidHCID 67305359HCID 67305359, Verbindung

Produkt 1

HCID 67305476HCID 67305476, Verbindung

Versuchsvorschrift

To a mixture of (2S,3S)-3-(tert-butoxycarbonyl)-5,5-difluoropiperidine-2-carboxylic acid (48 mg, 0.00018 mol) and 2,6-dimethyl-4-(1,2,3,6-tetrahydropyridin-4-yl)benzonitrile hydrochloride (84.7 mg, 0.000217 mol) TFA salt in N,N-dimethylformamide (0.406 mL, 0.00524 mol) was added benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (96.0 mg, 0.000217 mol), followed by N,N-diisopropylethylamine (0.0756 mL, 0.000434 mol). The mixture was stirred at rt overnight, then quenched with aq. sodium bicarbonate. The mixture was extracted with EtOAc. The combined organic layers were washed with water, brine, dried, and evaporated to dry. The residue was used directly in next step without further purification. LCMS (M+H) 460.2.

Aufarbeitung

  1. customquenched with aq. sodium bicarbonate
  2. extractionThe mixture was extracted with EtOAc
  3. washThe combined organic layers were washed with water, brine
  4. customdried
  5. customevaporated
  6. customto dry
  7. customThe residue was used directly in next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-92e5151923834de78f0c162fc7064500
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853243B2

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