Diisopropylethylamine → Tert-butyl 3-(4-(4-cyano-2-(2,6-difluorophenyl)oxazol-5-ylamino)phenylamino)-3-oxopropyl(methyl)carbamate

HRID 389784Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 389784
[C:1]([O:5][C:6]([N:8]([CH3:14])[CH2:9][CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[NH2:48][C:49]1[CH:54]=[CH:53][C:52]([NH:55][C:56]2[O:60][C:59]([C:61]3[C:66]([F:67])=[CH:65][CH:64]=[CH:63][C:62]=3[F:68])=[N:58][C:57]=2[C:69]#[N:70])=[CH:51][CH:50]=1>CN(C=O)C>[C:69]([C:57]1[N:58]=[C:59]([C:61]2[C:62]([F:68])=[CH:63][CH:64]=[CH:65][C:66]=2[F:67])[O:60][C:56]=1[NH:55][C:52]1[CH:51]=[CH:50][C:49]([NH:48][C:11](=[O:13])[CH2:10][CH2:9][N:8]([CH3:14])[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[CH:54][CH:53]=1)#[N:70]

Komponenten

6

Edukt 4

HCID 81531Diisopropylethylamine2×HCID 27609523-(Methylamino)propanoic acid, N-BOC protected2×HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)2×HCID 595874505-(4-Aminophenylamino)-2-(2,6-difluorophenyl)oxazole-4-carbonitrile

Produkt 1

HCID 59587674Tert-butyl 3-(4-(4-cyano-2-(2,6-difluorophenyl)oxazol-5-ylamino)phenylamino)-3-oxopropyl(methyl)carbamateAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of N-(tert-butoxycarbonyl)-3-methylaminopropanoic acid (0.022 g, 0.11 mmol) in DMF (1.25 ml) were added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.040 g, 0.11 mmol) and diisopropylethylamine (0.018 ml, 0.11 mmol) followed by 5-(4-aminophenylamino)-2-(2,6-difluorophenyl)oxazole-4-carbonitrile (0.030 g, 0.10 mmol) and the resultant mixture stirred at room temperature overnight. A further portion of N-(tert-butoxycarbonyl)-3-methylaminopropanoic acid (0.022 g, 0.11 mmol), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (0.040 g, 0.11 mmol) and diisopropylethylamine (0.018 ml, 0.11 mmol) was added and the reaction stirred for 2 hours at room temperature. The solvent was removed in vacuo and the residue purified by preparative HPLC to afford tert-butyl 3-(4-(4-cyano-2-(2,6-difluorophenyl)oxazol-5-ylamino)phenylamino)-3-oxopropyl(methyl)carbamate (0.021 g, 0.04 mmol, 44%) as a white solid. LCMS (2) Rt: 3.03 min; m/z (ES+) 498.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-63b87d4c2d134901b555e0ee17ba47b0
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08378095B2

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