Triethylamine → 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-N-((5-fluoropyridin-3-yl)methyl)-4-methylthiazole-5-carboxamide

HRID 1882451Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1882451
[CH:1]1([CH2:4][N:5]2[CH2:9][CH2:8][N:7]([C:10]3[S:11][C:12]([C:16]([OH:18])=O)=[C:13]([CH3:15])[N:14]=3)[C:6]2=[O:19])[CH2:3][CH2:2]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(CC)CC)C.[F:51][C:52]1[CH:53]=[C:54]([CH2:58][NH2:59])[CH:55]=[N:56][CH:57]=1>CN(C)C=O.C(OCC)(=O)C>[CH:1]1([CH2:4][N:5]2[CH2:9][CH2:8][N:7]([C:10]3[S:11][C:12]([C:16]([NH:59][CH2:58][C:54]4[CH:55]=[N:56][CH:57]=[C:52]([F:51])[CH:53]=4)=[O:18])=[C:13]([CH3:15])[N:14]=3)[C:6]2=[O:19])[CH2:2][CH2:3]1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 45116207(5-Fluoropyridin-3-yl)methanamineHCID 579198202-(3-(Cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

Produkt 1

HCID 579200012-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-N-((5-fluoropyridin-3-yl)methyl)-4-methylthiazole-5-carboxamideAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 2-(3-(cyclopropylmethyl)-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid (1.00 g, 3.55 mmol), 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU, 1.70 g, 4.47 mmol) and triethylamine (1.00 mL, 7.17 mmol) in N,N-dimethylformamide (15 mL) was added (5-fluoropyridin-3-yl)methanamine (0.55 g, 4.36 mmol). The reaction mixture was stirred at ambient temperature for 20 h, diluted with ethyl acetate (200 mL) and washed with water and brine. The organic solution was dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was recrystallized from ethyl acetate to afford the title compound as a white powder in 47% yield (0.65 g): mp 144-145° C.; 1H NMR (300 MHz, DMSO-d6) δ 8.53 (J=6.0 Hz, 1H), 8.43-8.38 (m, 2H), 7.59-7.56 (m, 1H), 4.39 (d, J=6.0 Hz, 2H), 4.00-3.95 (m, 2H), 3.64-3.59 (m, 2H), 3.06 (d, J=6.0 Hz, 2H), 2.44 (s, 3H), 0.95-0.87 (m, 1H), 0.48-0.42 (m, 2H), 0.20-0.16 (m, 2H); 13C NMR (75 MHz, DMSO-d6) δ 162.4, 161.1, 157.9, 155.2, 145.5, 137.9, 136.6, 122.5, 122.3, 117.6, 48.2, 42.5, 42.3, 40.8, 17.6, 9.3, 3.6; MS (ES+) m/z 389.9 (M+1).

Aufarbeitung

  1. washwashed with water and brine
  2. dry with materialThe organic solution was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was recrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-3372e1a5c81e4dc49bd178b70144070f
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08318949B2

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