Diisopropylethylamine → (+/-)-3-({6-[1-(3-Trifluoromethyl-phenylcarbamoyl)-1H-indol-5-yloxy]-pyrimidin-4-ylmethyl}-amino)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 450264Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 450264
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([N:12]2[C:20]3[C:15](=[CH:16][C:17]([O:21][C:22]4[N:27]=[CH:26][N:25]=[C:24]([CH2:28]OS(C)(=O)=O)[CH:23]=4)=[CH:18][CH:19]=3)[CH:14]=[CH:13]2)=[O:11])[CH:6]=[CH:7][CH:8]=1.[C:36]([O:40][C:41]([N:43]1[CH2:47][CH2:46][CH:45]([NH2:48])[CH2:44]1)=[O:42])([CH3:39])([CH3:38])[CH3:37].C(N(C(C)C)CC)(C)C>C1COCC1.CCOC(C)=O>[C:36]([O:40][C:41]([N:43]1[CH2:47][CH2:46][CH:45]([NH:48][CH2:28][C:24]2[CH:23]=[C:22]([O:21][C:17]3[CH:16]=[C:15]4[C:20](=[CH:19][CH:18]=3)[N:12]([C:10](=[O:11])[NH:9][C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:35])([F:34])[F:1])[CH:4]=3)[CH:13]=[CH:14]4)[N:27]=[CH:26][N:25]=2)[CH2:44]1)=[O:42])([CH3:39])([CH3:37])[CH3:38]

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 27563701-Boc-3-aminopyrrolidineHCID 46224264methanesulfonic acid 6-[1-(3-trifluoromethyl-phenylcarbamoyl)-1H-indol-5-yloxy]-pyrimidin-4-ylmethyl ester

Produkt 1

HCID 59394560(+/-)-3-({6-[1-(3-Trifluoromethyl-phenylcarbamoyl)-1H-indol-5-yloxy]-pyrimidin-4-ylmethyl}-amino)-pyrrolidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To the solution of methanesulfonic acid (±)-6-[1-(3-trifluoromethyl-phenylcarbamoyl)-1H-indol-5-yloxy]-pyrimidin-4-ylmethyl ester (80 mg, 0.158 mmol) in THF (5 mL), 3-amino-pyrrolidine-1-carboxylic acid tert-butyl ester (88 mg, 0.474 mmol) and diisopropylethylamine (61 mg, 0.474 mmol) are added. The resulting solution is stirred at 60° C. overnight. After cooling to rt, the reaction mixture is diluted with EtOAc and washed with water and then brine. The organic layer is dried with anhydrous Na2SO4, filtered, and condensed. The residue is purified by FCC (0-10% MeOH/DCM) to provide the title compound. MS (ESI) m/z 597.2 (M+1).

Aufarbeitung

  1. temperatureAfter cooling to rt
  2. washwashed with water
  3. dry with materialThe organic layer is dried with anhydrous Na2SO4
  4. filtrationfiltered
  5. customcondensed
  6. customThe residue is purified by FCC (0-10% MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-886e214340a44d59a4d2efb2de2fecfa
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08486954B2

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