Trifluoroacetic acid → HCID 44253045, Verbindung

HRID 1645248Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1645248
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2([CH2:21][CH2:22][CH2:23][N:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[CH2:13][CH2:12][N:11]([C:14](OC(C)(C)C)=[O:15])[CH2:10][CH2:9]2)[CH:5]=[CH:6][CH:7]=1.C(O)(C(F)(F)F)=O.[Cl:36][C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([CH3:43])[C:38]=1[S:44]([N:47]([CH2:51][CH2:52][O:53][CH2:54]C(O)=O)[CH:48]1[CH2:50][CH2:49]1)(=[O:46])=[O:45].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>ClCCl>[Cl:36][C:37]1[CH:42]=[CH:41][CH:40]=[C:39]([CH3:43])[C:38]=1[S:44]([N:47]([CH2:51][CH2:52][O:53][CH2:54][C:14]([N:11]1[CH2:10][CH2:9][C:8]([C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=2)([CH2:21][CH2:22][CH2:23][N:24]2[CH2:25][CH2:26][CH2:27][CH2:28]2)[CH2:13][CH2:12]1)=[O:15])[CH:48]1[CH2:50][CH2:49]1)(=[O:46])=[O:45]

Komponenten

8

Edukt 6

HCID 6422Trifluoroacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 57916235HCID 57916235, VerbindungHCID 57917551HCID 57917551, Verbindung

Produkt 1

HCID 44253045HCID 44253045, VerbindungAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Versuchsvorschrift

A solution of tert-butyl 4-(3-chlorophenyl)-4-(3-(pyrrolidin-1-yl)propyl)piperidine-1-carboxylate (0.15 g, 0.37 mmol) in dichloromethane (3 ml) was Boc-deprotected using standard reaction conditions (see step (vi)/example 25; TFA (3-13 eq.)) and added dropwise to a solution containing 2-(2-(2-chloro-N-cyclopropyl-6-methylphenylsulfonamido)ethoxy)acetic acid [carboxylic acid 2] (1 eq.), EDCI (1.5 eq.), HOBt (1 eq.) and DIPEA (6 eq.) in dichloromethane (5 ml) at 0° C. The resulting mixture was then stirred at room temperature for 16 h. The reaction mixture was diluted with dichloromethane and washed with aq. ammonium chloride, aq. sodium hydrogen carbonate and water respectively. The organic layer was dried over sodium sulfate, concentrated in vacuo and the crude product purified by chromatography (silica). Yield: 25%

Aufarbeitung

  1. customBoc-deprotected using standard reaction conditions (
  2. additionadded dropwise to a solution
  3. washwashed with aq. ammonium chloride, aq. sodium hydrogen carbonate and water respectively
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customthe crude product purified by chromatography (silica)

Quellen und Nachweise

ORD-Eintrag
ord-2c242f5b887540b797d7212d89acc5fb
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08124624B2

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