Triethylamine → HCID 24950096, Verbindung

HRID 625035Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 625035
Cl.Cl.[CH3:3][C@H:4]1[C:12]2[C:11]([N:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[N:10][CH:9]=[N:8][C:7]=2[CH2:6][S:5]1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]([CH2:30][N:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)[C:27](O)=[O:28])=[CH:22][CH:21]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)CC)C>C(Cl)Cl>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]([CH2:30][N:31]2[CH2:32][CH2:33][CH2:34][CH2:35]2)[C:27]([N:16]2[CH2:17][CH2:18][N:13]([C:11]3[C:12]4[C@H:4]([CH3:3])[S:5][CH2:6][C:7]=4[N:8]=[CH:9][N:10]=3)[CH2:14][CH2:15]2)=[O:28])=[CH:22][CH:21]=1

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 673399992-(4-Chlorophenyl)-3-(pyrrolidin-1-yl)propanoic acidHCID 67459940HCID 67459940, Verbindung

Produkt 1

HCID 24950096HCID 24950096, VerbindungAusbeute 46,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (S)-5-methyl-4-(piperazin-1-yl)-5,7-dihydrothieno[3,4-d]pyrimidine dihydrochloride (1 g, 3.23 mmol) and 2-(4-chlorophenyl)-3-(pyrrolidin-1-yl)propanoic acid (2 g, 7.88 mmol) in DCM (40 mL) were added HBTU (1.5 g, 3.96 mmol) and triethylamine (2.75 mL, 19.8 mmol). The mixture was stirred at room temperature for 1 hour. The solvent was removed, and the residue was dissolved in ethyl acetate (200 mL) and washed with brine (5×100 mL) and water (3×100 mL). The organic phase was dried and concentrated. The residue was purified by silica gel chromatography, eluting with ethyl acetate-DCM/MeOH (20:1) to give 2-(4-chlorophenyl)-1-(4-((S)-5-methyl-5,7-dihydrothieno[3,4-d]pyrimidin-4-yl)piperazin-1-yl)-3-(pyrrolidin-1-yl)propan-1-one (0.713 g, 46.7%). 1H NMR (CDCl3, 400 MHz) δ 8.47 (s, 1H), 7.38-7.28 (m, 4H), 4.75 (m, 1H), 4.54 (m, 1H), 4.17 (m, 2H), 3.88-3.25 (m, 14H), 2.12 (m, 4H), 1.43 (m, 3H). MS (APCI+) [M+H]+ 473.

Aufarbeitung

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in ethyl acetate (200 mL)
  3. washwashed with brine (5×100 mL) and water (3×100 mL)
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with ethyl acetate-DCM/MeOH (20:1)

Quellen und Nachweise

ORD-Eintrag
ord-e1002aaea4754928a5e113cd324cbf35
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09303040B2

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