1,1'-Carbonyldiimidazole → 1-(8-((4-(2-Hydroxypropan-2-yl)piperidin-1-yl)methyl)-9-methyl-6-morpholino-9h-purin-2-yl)-1h-benzo[d]imidazol-2(3h)-one

HRID 1922916Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1922916
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[N:17]=[C:16]2[C:12]([N:13]=[C:14]([CH2:19][N:20]3[CH2:25][CH2:24][CH:23]([C:26]([OH:29])([CH3:28])[CH3:27])[CH2:22][CH2:21]3)[N:15]2[CH3:18])=[C:11]([N:30]2[CH2:35][CH2:34][O:33][CH2:32][CH2:31]2)[N:10]=1.C1N=CN([C:41](N2C=NC=C2)=[O:42])C=1>C(#N)C>[OH:29][C:26]([CH:23]1[CH2:22][CH2:21][N:20]([CH2:19][C:14]2[N:15]([CH3:18])[C:16]3[C:12]([N:13]=2)=[C:11]([N:30]2[CH2:31][CH2:32][O:33][CH2:34][CH2:35]2)[N:10]=[C:9]([N:8]2[C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=4[NH:1][C:41]2=[O:42])[N:17]=3)[CH2:25][CH2:24]1)([CH3:28])[CH3:27]

Komponenten

4

Edukt 2

HCID 682631,1'-CarbonyldiimidazoleHCID 596059592-(1-((2-(2-aminophenylamino)-9-methyl-6-morpholino-9H-purin-8-yl)methyl)piperidin-4-yl)propan-2-ol

Produkt 1

HCID 498343951-(8-((4-(2-Hydroxypropan-2-yl)piperidin-1-yl)methyl)-9-methyl-6-morpholino-9h-purin-2-yl)-1h-benzo[d]imidazol-2(3h)-oneAusbeute 16 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of 2-(1-((2-(2-aminophenylamino)-9-methyl-6-morpholino-9H-purin-8-yl)methyl)piperidin-4-yl)propan-2-ol (40 mg, 0.083 mmol) and N,N-carbonyldiimidazole (17 mg, 0.108 mmol) in acetonitrile (2 mL) was stirred at reflux for 15 hours. The reaction mixture was then filtered through paper and purified by RP-HPLC to give 156 (6.7 mg, 16%). LCMS: M+H+=507.2. 1H-NMR (400 MHz, DMSO-d6): δ 11.0 (s, 1H), 7.55 (d, 1H), 7.04 (m, 3H), 4.21 (s, br, 4H), 4.02 (s, 1H), 3.78 (s, 3H), 3.74 (m, 6H), 2.88 (m, 2H), 2.00 (m, 2H), 1.66 (m, 2H), 1.20 (m, 3H), 1.02 (s, 6H)

Aufarbeitung

  1. temperatureat reflux for 15 hours
  2. filtrationThe reaction mixture was then filtered through paper
  3. custompurified by RP-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-cd93c63980c24e66aa5a587be324cb55
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173650B2

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