1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 53246993, Verbindung

HRID 1476534Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1476534
FC(F)(F)C(O)=O.[CH2:8]([N:10]1[N:14]=[C:13]([CH2:15][N:16]2[C:21]3[CH:22]=[C:23]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[S:24][C:20]=3[C:19](=[O:31])[N:18]([CH:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[C:17]2=[O:38])[CH:12]=[N:11]1)[CH3:9].[CH2:39]([O:41][C:42]1[C:51]([O:52][CH3:53])=[CH:50][C:49]2[C:48]([C:54]3[CH:62]=[CH:61][C:57]([C:58](O)=[O:59])=[CH:56][CH:55]=3)=[N:47][C@@H:46]3[CH2:63][CH2:64][S:65][CH2:66][C@@H:45]3[C:44]=2[CH:43]=1)[CH3:40].CCN=C=NCCCN(C)C.C1C=C2N=NN(O)C2=CC=1.O.S([O-])(O)(=O)=O.[K+]>C(Cl)Cl.O>[CH2:39]([O:41][C:42]1[C:51]([O:52][CH3:53])=[CH:50][C:49]2[C:48]([C:54]3[CH:55]=[CH:56][C:57]([C:58]([N:35]4[CH2:36][CH2:37][CH:32]([N:18]5[C:19](=[O:31])[C:20]6[S:24][C:23]([C:25]7[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=7)=[CH:22][C:21]=6[N:16]([CH2:15][C:13]6[CH:12]=[N:11][N:10]([CH2:8][CH3:9])[N:14]=6)[C:17]5=[O:38])[CH2:33][CH2:34]4)=[O:59])=[CH:61][CH:62]=3)=[N:47][C@@H:46]3[CH2:63][CH2:64][S:65][CH2:66][C@@H:45]3[C:44]=2[CH:43]=1)[CH3:40]

Komponenten

8

Edukt 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 516920Potassium bisulfateHCID 27960291-Hydroxybenzotriazole hydrateHCID 67259075HCID 67259075, Verbindung2×HCID 672590924-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid

Produkt 1

HCID 53246993HCID 53246993, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a suspension of 1-[(2-ethyl-2H-1,2,3-triazol-4-yl)methyl]-6-phenyl-3-(piperidin-4-yl)thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione trifluoroacetate (300 mg; compound B45), 4-[(4aR,10bR)-9-ethoxy-8-methoxy-3,4,4a,10b-tetrahydro-1H-thiopyrano[4,3-c]isoquinolin-6-yl]benzoic acid (217 mg; compound C10), EDCI (104 mg) and HOBT hydrate (74 mg) in DCM (10 ml) DIPEA (0.24 ml) is added. After 14 h at RT water and aqueous potassium hydrogen sulfate solution (10% w/w) are added and the mixture is extracted with DCM. The combined organic layers are dried (sodium sulfate) and concentrated under reduced pressure. The residue is purified by twofold flash column chromatography [silica gel, eluation gradient: DCM/MeOH, 1/0 to 1/1 (v/v)] and preparative HPLC to afford the title compound as a solid.

Aufarbeitung

  1. additionis added
  2. extractionthe mixture is extracted with DCM
  3. dry with materialThe combined organic layers are dried (sodium sulfate)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by twofold flash column chromatography [silica gel, eluation gradient: DCM/MeOH, 1/0 to 1/1 (v/v)] and preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-a68a85cc6c574dcea9b73e202d56c6a9
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09018175B2

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