4-Methylmorpholine → 5-{5-[2-Methyl-5-(3-Trifluoromethyl-Benzoylamino)-Benzoylamino]-Pyrimidin-2-ylamino}-Pyridine-2-Carboxylic Acid (2-Pyrrolidin-1-yl-Ethyl)-Amide

HRID 1662821Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1662821
[F:1][C:2]([F:23])([F:22])[C:3]1[CH:4]=[C:5]([CH:19]=[CH:20][CH:21]=1)[C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:18])=[C:13]([CH:17]=1)[C:14]([OH:16])=O)=[O:7].ClC1N=C(OC)N=C(OC)N=1.CN1CCOCC1.[N:42]1([CH2:47][CH2:48][NH:49][C:50]([C:52]2[CH:57]=[CH:56][C:55]([NH:58][C:59]3[N:64]=[CH:63][C:62]([NH2:65])=[CH:61][N:60]=3)=[CH:54][N:53]=2)=[O:51])[CH2:46][CH2:45][CH2:44][CH2:43]1>C(Cl)Cl>[N:42]1([CH2:47][CH2:48][NH:49][C:50]([C:52]2[CH:57]=[CH:56][C:55]([NH:58][C:59]3[N:60]=[CH:61][C:62]([NH:65][C:14](=[O:16])[C:13]4[CH:17]=[C:9]([NH:8][C:6](=[O:7])[C:5]5[CH:19]=[CH:20][CH:21]=[C:3]([C:2]([F:1])([F:23])[F:22])[CH:4]=5)[CH:10]=[CH:11][C:12]=4[CH3:18])=[CH:63][N:64]=3)=[CH:54][N:53]=2)=[O:51])[CH2:46][CH2:45][CH2:44][CH2:43]1

Komponenten

6

Edukt 4

HCID 79724-MethylmorpholineHCID 184502-Chloro-4,6-dimethoxy-1,3,5-triazineHCID 587487255-(5-Amino-pyrimidin-2-ylamino)-pyridine-2-carboxylic acid (2-Pyrrolidin-1-yl-ethyl)-amideHCID 596527072-Methyl-5-{[3-(trifluoromethyl)benzoyl]amino}benzoic acid

Produkt 1

HCID 249614635-{5-[2-Methyl-5-(3-Trifluoromethyl-Benzoylamino)-Benzoylamino]-Pyrimidin-2-ylamino}-Pyridine-2-Carboxylic Acid (2-Pyrrolidin-1-yl-Ethyl)-AmideAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Intermediate 3 (Example 5) (0.070 g, 0.215 mmol) was combined with 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) (0.046 g, 0.26 mmol) and diluted with DCM (4 mL). This was immediately treated with 4-methyl morpholine (0.05 mL, 0.43 mmol) and allowed to stir at ambient temperature for 1 h. Intermediate 23 (Example 31) (0.074 g, 0.226 mmol) was then added in one portion. Stirring was continued overnight. After 18 h, reaction solvents were removed and resulting crude solids purified via HPLC to afford the title compound as a white solid (0.027 g, 20%).

Aufarbeitung

  1. stirringStirring
  2. waitwas continued overnight
  3. waitAfter 18 h
  4. customreaction solvents
  5. customwere removed
  6. customresulting crude solids
  7. custompurified via HPLC

Quellen und Nachweise

ORD-Eintrag
ord-701fb3532766498e9ca92d6610c40a7f
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030487B2

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