Cyclobutylamine → (trans)-N-cyclobutyl-2-{4-[({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)amino]phenyl}cyclopropanecarboxamide

HRID 1173026

Reaktionsgleichung

Reaktionsgleichung von HRID 1173026
CN(C(ON1N=[N:16][C:11]2[CH:12]=[CH:13][CH:14]=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:25][C:26]1[N:27]=[C:28]([C:45]2[CH:50]=[CH:49][C:48]([C:51]([F:54])([F:53])[F:52])=[CH:47][CH:46]=2)[S:29][C:30]=1[CH2:31][NH:32][C:33]1[CH:38]=[CH:37][C:36]([C@@H:39]2[CH2:41][C@H:40]2[C:42](O)=[O:43])=[CH:35][CH:34]=1.C1(N)CCC1.C([O-])(O)=O.[Na+]>CN(C=O)C>[CH:11]1([NH:16][C:42]([C@@H:40]2[CH2:41][C@H:39]2[C:36]2[CH:37]=[CH:38][C:33]([NH:32][CH2:31][C:30]3[S:29][C:28]([C:45]4[CH:50]=[CH:49][C:48]([C:51]([F:52])([F:54])[F:53])=[CH:47][CH:46]=4)=[N:27][C:26]=3[CH3:25])=[CH:34][CH:35]=2)=[O:43])[CH2:12][CH2:13][CH2:14]1

Komponenten

6

Edukt 4

HCID 75645CyclobutylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11487291(+)-(trans)-2-{4-[({4-Methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)amino]phenyl}cyclopropanecarboxylic acid

Produkt 1

HCID 11237091(trans)-N-cyclobutyl-2-{4-[({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)amino]phenyl}cyclopropanecarboxamideAusbeute 77,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

HATU (0.154 g, 0.41 mmol) and (+)-(trans)-2-{4-[({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)amino]phenyl}cyclopropanecarboxylic acid (III-3c) (0.135 g, 0.31 mmol) in DMF (10 mL) were stirred at RT for 15 min, then cyclobutylamine (0.50 g) was added. The solution was stirred at RT for 1 h, then saturated NaHCO3 solution (20 mL) was added. The resulting solid was filtered, washed with water (10 mL) and dissolved in ethyl acetate (50 mL). The organic layer was dried over MgSO4, filtered and concentrated to give the title compound as a white powder (0.116 g, 77%). 1H NMR (400 MHz, DMSO) δ8.23 (d, J=7.5 Hz, 1H), 8.01 (d, J=8.1 Hz, 2H), 7.76 (d, J=8.0 Hz, 2H), 6.81 (d, J=8.3 Hz, 2H), 6.51 (d, J=8.4 Hz, 2H), 6.20 (t, J=5.8 Hz, 1H), 4.38 (d, J=5.5 Hz, 2H), 4.19-4.13 (m, 1H), 2.42 (s, 3H), 2.10-2.06 (m, 2H), 2.04-1.99 (m, 1H), 1.85-1.75 (m, 2H), 1.59-1.50 (m, 3H), 1.18-1.13 (m, 1H), 1.01-0.96 (m, 1H).

Aufarbeitung

  1. filtrationThe resulting solid was filtered
  2. washwashed with water (10 mL)
  3. dissolutiondissolved in ethyl acetate (50 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-efe4f08e0991467ebde83ab4f970e56c
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834013B2

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