Triethylamine → (2,2-dimethyl-4-(methylsulfonyl)piperazin-1-yl)(2-(2-ethyl-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)methanone

HRID 1923320Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1923320
[CH2:1]([C:3]1[N:7]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[C:13]([C:18](O)=[O:19])[N:14]3[CH3:17])=[C:10]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)[N:9]=2)[C:6]2[CH:27]=[CH:28][CH:29]=[CH:30][C:5]=2[N:4]=1)[CH3:2].[CH3:31][S:32]([N:35]1[CH2:40][CH2:39][NH:38][C:37]([CH3:42])([CH3:41])[CH2:36]1)(=[O:34])=[O:33].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>CN(C=O)C>[CH3:41][C:37]1([CH3:42])[CH2:36][N:35]([S:32]([CH3:31])(=[O:33])=[O:34])[CH2:40][CH2:39][N:38]1[C:18]([C:13]1[N:14]([CH3:17])[C:15]2[C:11]([N:12]=1)=[C:10]([N:21]1[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1)[N:9]=[C:8]([N:7]1[C:6]3[CH:27]=[CH:28][CH:29]=[CH:30][C:5]=3[N:4]=[C:3]1[CH2:1][CH3:2])[N:16]=2)=[O:19]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 198151421-Methanesulfonyl-3,3-dimethylpiperazineHCID 596053252-(2-ethyl-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purine-8-carboxylic acid

Produkt 1

HCID 59606151(2,2-dimethyl-4-(methylsulfonyl)piperazin-1-yl)(2-(2-ethyl-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purin-8-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 2-(2-ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine-8-carboxylic acid (117 mg, 0.26 mmol), 1-methanesulfonyl-3,3-dimethylpiperazine (51 mg, 0.26 mmol) and HATU (100 mg, 0.26 mmol) in DMF (1 mL) was added NEt3 (720 μL, 5.18 mmol). The resulting mixture was allowed to stir at r.t. for 16 h then partitioned between EtOAc and H2O. The organic phase was dried (MgSO4) and concentrated in vacuo and the resulting residue was purified by column chromatography (Si—PCC, MeOH:EtOAc, 0-5%). The resulting solid was recrystallised from EtOAc and Et2O affording 715 (50 mg, 33%). LCMS (method I): RT 3.68 min, [M+H]+ 582.2. 1H NMR (CDCl3, 400 MHz): δ 8.03-8.03 (1 H, m), 7.76-7.75 (1 H, m), 7.31-7.27 (2 H, m), 4.35 (4 H, brd s), 4.03 (2 H, t, J=5.39 Hz), 3.95 (3 H, s), 3.87 (4 H, t, J=4.70 Hz), 3.50 (2 H, t, J=5.40 Hz), 3.37 (2 H, q, J=7.47 Hz), 3.31 (2 H, s), 2.90 (3 H, s), 1.68 (6 H, s), 1.45 (3 H, t, J=7.47 Hz)

Aufarbeitung

  1. customthen partitioned between EtOAc and H2O
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customthe resulting residue was purified by column chromatography (Si—PCC, MeOH:EtOAc, 0-5%)
  5. customThe resulting solid was recrystallised from EtOAc and Et2O affording 715 (50 mg, 33%)
  6. customRT 3.68 min, [M+H]+ 582.2

Quellen und Nachweise

ORD-Eintrag
ord-466ae7fdfd024683a79ad1cce249d708
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173650B2

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