N,N-Diisopropylmethylamine → HCID 68157281, Verbindung

HRID 243338

Reaktionsgleichung

Reaktionsgleichung von HRID 243338
[C:1]1([N:7]2[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=3[N:9]=[C:8]2[C@@H:16]([NH2:18])[CH3:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:20]1[N:21]=[CH:22][C:23]2[N:28]([CH3:29])[N:27]=[CH:26][C:24]=2[N:25]=1.CN(C(C)C)C(C)C>C(O)CCC>[CH3:29][N:28]1[C:23]2[CH:22]=[N:21][C:20]([NH:18][C@H:16]([C:8]3[N:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)[C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=4[N:9]=3)[CH3:17])=[N:25][C:24]=2[CH:26]=[N:27]1

Komponenten

5

Edukt 3

HCID 547370N,N-DiisopropylmethylamineHCID 68157455(1S)-1-(1-Phenyl-1H-benzimidazol-2-yl)ethan-1-amineHCID 71743115HCID 71743115, Verbindung

Produkt 1

HCID 68157281HCID 68157281, VerbindungAusbeute 35,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

A solution of (S)-1-(1-phenyl-1H-benzo[d]imidazol-2-yl)ethanamine from Example 4 (200 mg, 0.83 mmol, 1.00 equiv, 98%), 5-chloro-1-methyl-1H-pyrazolo[4,3-d]pyrimidine (180 mg, 1.07 mmol, 1.29 equiv) and methylbis(propan-2-yl)amine (0.3 mL, 98%) in n-butanol (8 mL) was stirred at 130° C. for 96 h. The resulting mixture was concentrated under vacuum and the residue was purified on a C18 column eluted with water/acetonitrile to give 110 mg (31%) of 159 as a light yellow solid. LC-MS: (ES, m/z) 370 [M+H]+, 221, 115. H-NMR: (CD3OD, 300 Hz, ppm) δ 8.86 (s, 1H), 7.70 (s, 1H), 7.65-7.54 (m, 6H), 7.61 (d, 2H), 7.09 (s, 1H), 5.30 (m, 1H), 4.04 (s, 3H), 1.64 (d, 3H)

Aufarbeitung

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. customthe residue was purified on a C18 column
  3. washeluted with water/acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-f9003da174fb4f9e8742a63982d0cd83
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08653089B2

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