Hydroxylamine → 4-Cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-yl-N-(tetrahydro-2H-pyran-2-yloxy)thiophene-2-carboxamide

HRID 572629Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 572629
[C:1]([C:3]1[C:4]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])=[C:5]([C:14]([OH:16])=O)[S:6][C:7]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)#[N:2].CN(C(ON1N=N[C:35]2[CH:36]=[CH:37][CH:38]=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.[NH2:58][OH:59].CN([CH:63]=[O:64])C>>[C:1]([C:3]1[C:4]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=2[Cl:24])=[C:5]([C:14]([NH:58][O:59][CH:38]2[CH2:37][CH2:36][CH2:35][CH2:63][O:64]2)=[O:16])[S:6][C:7]=1[N:8]1[CH2:9][CH2:10][O:11][CH2:12][CH2:13]1)#[N:2]

Komponenten

6

Edukt 5

HCID 787HydroxylamineHCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 441556654-Cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxylic acid

Produkt 1

HCID 866375484-Cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-yl-N-(tetrahydro-2H-pyran-2-yloxy)thiophene-2-carboxamideAusbeute 55 %

Versuchsvorschrift

4-Cyano-3-(2,4-dichlorophenyl)-5-morpholin-4-ylthiophene-2-carboxylic acid (0.080 g, 0.21 mmol), HATU (0.095 g, 0.25 mmol), and diisopropylethylamine (0.073 mL, 0.42 mmol) were dissolved in DMF (2 mL) and stirred for 30 minutes. O-Tetrahydropyran-2-yl)hydroxylamine (0.049 g, 0.42 mmol) was added and the mixture was stirred at room temperature. After 30 minutes, LCMS showed complete conversion. Reaction was quenched by addition of water (5 mL) and the precipitate was filtered off, washed with water (2 mL) and hexane (5 mL) and dried to afford the title compound (0.055 g, 55%).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature
  2. waitAfter 30 minutes
  3. customReaction
  4. customwas quenched by addition of water (5 mL)
  5. filtrationthe precipitate was filtered off
  6. washwashed with water (2 mL) and hexane (5 mL)
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-6e2604004e0f4aaf82d86d57b695d067
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029411B2

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