Diisopropylethylamine → 2-[2-(3-Trifluoromethyl-4,5,6,7-tetrahydroindazol-1-yl)-acetylamino]-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid tert-butyl ester

HRID 1162737Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1162737
[F:1][C:2]([F:17])([F:16])[C:3]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:5]([CH2:12][C:13]([OH:15])=O)[N:4]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.CCN(C(C)C)C(C)C.[C:51]([O:55][C:56]([C:58]1[C:59]2[CH2:67][CH2:66][CH2:65][CH2:64][C:60]=2[S:61][C:62]=1[NH2:63])=[O:57])([CH3:54])([CH3:53])[CH3:52]>CN(C=O)C.C(Cl)Cl>[C:51]([O:55][C:56]([C:58]1[C:59]2[CH2:67][CH2:66][CH2:65][CH2:64][C:60]=2[S:61][C:62]=1[NH:63][C:13](=[O:15])[CH2:12][N:5]1[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[C:3]([C:2]([F:1])([F:17])[F:16])=[N:4]1)=[O:57])([CH3:54])([CH3:52])[CH3:53]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 788039[3-(trifluoromethyl)-4,5,6,7-tetrahydro-1H-indazol-1-yl]acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 10777280tert-Butyl 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylate

Produkt 1

HCID 595204592-[2-(3-Trifluoromethyl-4,5,6,7-tetrahydroindazol-1-yl)-acetylamino]-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid tert-butyl esterAusbeute 75,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(3-Trifluoromethyl-4,5,6,7-tetrahydroindazol-1-yl)-acetic acid (638 mg, 2.57 mmol) was suspended in a solution of DCM (10 mL) and DMF (1 mL) and O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (1.17 g, 3.08 mmol) and N,N′-diisopropylethylamine (537 μL, 3.08 mmol) added, followed by 2-Amino-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid tert-butyl ester (651 mg, 2.57 mmol). The resultant mixture was stirred at RT overnight. The solution was concentrated in vacuo. The residue was purified by silica gel chromatography using DCM as eluent, to afford the title compound as a yellow solid (0.93 g, 1.93 mmol, 75%).

Aufarbeitung

  1. additionadded
  2. concentrationThe solution was concentrated in vacuo
  3. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-95ccfd06898a450abfd5b508ffb59f9a
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07820707B2

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