Isopropylamine → Racemic-(trans)-n-isopropyl-2-{4-[({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)amino]phenyl}cyclopropanecarboxamide

HRID 1173028

Reaktionsgleichung

Reaktionsgleichung von HRID 1173028
[CH3:1][C:2]1[N:3]=[C:4]([C:21]2[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=2)[S:5][C:6]=1[CH2:7][NH:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]2[CH2:17][C@H:16]2[C:18]([OH:20])=O)=[CH:11][CH:10]=1.CN(C(ON1N=[N:46][C:41]2[CH:42]=CC=N[C:40]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N)(C)C>ClCCl.CN(C=O)C>[CH:41]([NH:46][C:18]([C@@H:16]1[CH2:17][C@H:15]1[C:12]1[CH:13]=[CH:14][C:9]([NH:8][CH2:7][C:6]2[S:5][C:4]([C:21]3[CH:22]=[CH:23][C:24]([C:27]([F:29])([F:30])[F:28])=[CH:25][CH:26]=3)=[N:3][C:2]=2[CH3:1])=[CH:10][CH:11]=1)=[O:20])([CH3:42])[CH3:40]

Komponenten

6

Edukt 3

HCID 6363IsopropylamineHCID 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 11202282Racemic-(trans)-n-isopropyl-2-{4-[({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)amino]phenyl}cyclopropanecarboxamideAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a mixture of racemic-(trans)-2-{4-[({4-methyl-2-[4-(trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methyl)amino]phenyl}cyclopropanecarboxylic acid (I-2m) (0.10 g, 0.231 mmol) in dichloromethane (2 mL) and DMF (1 mL) was added HATU (0.13 g, 0.346 mmol). The mixture was stirred for 15 mins followed by addition of isopropylamine (0.04 g, 0.693 mmol). The solution stirred for 6 h after which the dichloromethane was removed via rotavap. Sat. NaHCO3 and ethyl acetate were added and the organic layer separated and washed with H2O, dried over MgSO4, filtered and concentrated. The resulting oil was triterated with Et2O and formed a yellow ppt which was filtered and dried under high vacuum to give the title compound as a yellow powder (0.062 g, 60%). 1H NMR (400 MHz, CDCl3) δ 7.98 (d, J=8.2 Hz, 2H), 7.66 (d, J=8.1 Hz, 2H), 6.96 (d, J=8.1 Hz, 2H), 6.59 (d, J=8.4 Hz, 2H), 5.29 (d, J=7.8 Hz, 1H), 4.45 (s, 2H), 4.15-4.08 (m, 1H), 4.06 (s, 1H), 2.49 (s, 3H), 2.42-2.34 (m, 1H), 1.54-1.51 (m, 1H), 1.44-1.39 (m, 1H), 1.53-1.10 (m, 7H).

Aufarbeitung

  1. customwas removed via rotavap
  2. additionSat. NaHCO3 and ethyl acetate were added
  3. customthe organic layer separated
  4. washwashed with H2O
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customformed a yellow ppt which
  9. filtrationwas filtered
  10. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5089287ad93943469d2bc59bf4e0260b
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07834013B2

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