Acetic Acid → 2-(1-((9-methyl-2-(2-methyl-1H-benzo[d]imidazol-1-yl)-6-morpholino-9H-purin-8-yl)methyl)piperidin-4-yl)propan-2-ol

HRID 1922918Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1922918
[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.[C:36](O)(=O)[CH3:37]>>[CH3:18][N:15]1[C:14]([CH2:19][N:20]2[CH2:21][CH2:22][CH:23]([C:26]([OH:29])([CH3:28])[CH3:27])[CH2:24][CH2:25]2)=[N:13][C:12]2[C:16]1=[N:17][C:9]([N:8]1[C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[N:1]=[C:36]1[CH3:37])=[N:10][C:11]=2[N:30]1[CH2:31][CH2:32][O:33][CH2:34][CH2:35]1

Komponenten

3

Edukt 2

HCID 176Acetic AcidHCID 596059592-(1-((2-(2-aminophenylamino)-9-methyl-6-morpholino-9H-purin-8-yl)methyl)piperidin-4-yl)propan-2-ol

Produkt 1

HCID 498343962-(1-((9-methyl-2-(2-methyl-1H-benzo[d]imidazol-1-yl)-6-morpholino-9H-purin-8-yl)methyl)piperidin-4-yl)propan-2-olAusbeute 21,1 %

Versuchsvorschrift

A mixture of 2-(1-((2-(2-aminophenylamino)-9-methyl-6-morpholino-9H-purin-8-yl)methyl)piperidin-4-yl)propan-2-ol (177 mg, 0.368 mmol) in acetic acid (1.5 mL) was stirred at reflux for 5 hours. The reaction mixture was then concentrated and then purified first by flash chromatography (10% MeOH in DCM containing 1% 2 M ammonia in MeOH), followed by RP-HPLC to give 157 (0.0373 g, 21.1%). LCMS: M+H+=505.3. 1H-NMR (400 MHz, DMSO-d6): δ 8.09 (m, 1H), 7.60 (m, 1H), 7.25 (m, 2H), 4.26 (s, br, 4H), 4.02 (s, 1H), 3.83 (s, 3H), 3.78 (m, 4H), 3,73 (s, 2H), 2.90 (m, 2H), 2.84 (s, 3H), 1.99 (m, 2H), 1.66 (m, 2H), 1.21 (m, 3H), 1.02 (s, 6H).

Aufarbeitung

  1. temperatureat reflux for 5 hours
  2. concentrationThe reaction mixture was then concentrated
  3. custompurified first by flash chromatography (10% MeOH in DCM containing 1% 2 M ammonia in MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-dcd4fee534ba42879fc8d782cfd5a4c2
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08173650B2

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