Hydrochloric Acid → (R)-2-(3-{2-[4-(2-Methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)hexahydro-3H-pyrrolo[1,2-c]imidazol-3-one

HRID 15897Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 15897
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([NH:26][CH2:27][CH:28]4[CH2:32][CH2:31][CH2:30][N:29]4[C:33]([O:35]C(C)(C)C)=O)[CH:23]=[CH:24][CH:25]=3)[CH2:14][CH2:13]2)[N:3]=1.Cl.ClC(Cl)(OC(=O)OC(Cl)(Cl)Cl)Cl.C(NC(C)C)(C)C>CO.CCOCC>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[N:12]2[CH2:13][CH2:14][N:15]([CH2:18][CH2:19][C:20]3[CH:21]=[C:22]([N:26]4[CH2:27][C@H:28]5[CH2:32][CH2:31][CH2:30][N:29]5[C:33]4=[O:35])[CH:23]=[CH:24][CH:25]=3)[CH2:16][CH2:17]2)[N:3]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 94429TriphosgeneHCID 765409851,1-Dimethylethyl 2-{[(3-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)amino]methyl}-1-pyrrolidinecarboxylate

Produkt 1

HCID 57463854(R)-2-(3-{2-[4-(2-Methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)hexahydro-3H-pyrrolo[1,2-c]imidazol-3-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of (R)-(1,1-dimethylethyl 2-{[(3-{2-[4-(2-methyl-5-quinolinyl)-1-piperazinyl]ethyl}phenyl)amino]methyl}-1-pyrrolidinecarboxylate in methanol was treated with a solution of hydrogen chloride in ether (1M). The resulting mixture was stirred 30 minutes then concentrated under vacuum and then loaded onto an ion-exchange cartridge (SCX-2) and eluted with methanol followed by ammonia in methanol (1 M). The combined basic fractions were concentrated under vacuum. The residue, (10 mg) was then dissolved in DCM (1 mL) and treated with triphosgene (23 mg, 0.3 eq.), diisopropylamine (4 uL, 3 eq.). The mixture was stirred for 1 h then concentrated under vacuum and purified by preparative mass-directed hplc to afford the title compound (3.1 mg).

Aufarbeitung

  1. concentrationthen concentrated under vacuum
  2. washeluted with methanol
  3. concentrationThe combined basic fractions were concentrated under vacuum
  4. dissolutionThe residue, (10 mg) was then dissolved in DCM (1 mL)
  5. stirringThe mixture was stirred for 1 h
  6. concentrationthen concentrated under vacuum
  7. custompurified by preparative mass-directed hplc

Quellen und Nachweise

ORD-Eintrag
ord-331648d55fa94256b6a3643d83c4757a
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732600B2

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