Triethylamine → 5-(8-(4-(1,4'-Bipiperidine-1'-carbonyl)phenylamino)imidazo[1,2-a]pyridin-5-yl)isoindolin-1-one

HRID 552395Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 552395
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]3[N:16]4[CH:17]=[CH:18][N:19]=[C:15]4[C:14]([NH:20][C:21]4[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=4)=[CH:13][CH:12]=3)=[CH:8][CH:9]=2)[CH2:4][NH:3]1.[CH3:30][N:31](C)[C:32]1C=CC(CN)=C[CH:33]=1.[CH2:41]([N:43]([CH2:46][CH3:47])[CH2:44][CH3:45])[CH3:42].F[P-](F)(F)(F)(F)F.N1(O[P+](N2CCCC2)(N2CCCC2)N2CCCC2)C2C=CC=C[C:58]=2N=N1>CN(C)C=O.CCOC(C)=O>[N:43]1([CH:46]2[CH2:33][CH2:32][N:31]([C:25]([C:24]3[CH:23]=[CH:22][C:21]([NH:20][C:14]4[C:15]5[N:16]([CH:17]=[CH:18][N:19]=5)[C:11]([C:7]5[CH:6]=[C:5]6[C:10](=[CH:9][CH:8]=5)[C:2](=[O:1])[NH:3][CH2:4]6)=[CH:12][CH:13]=4)=[CH:29][CH:28]=3)=[O:26])[CH2:30][CH2:47]2)[CH2:44][CH2:45][CH2:58][CH2:42][CH2:41]1

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 808264-(Aminomethyl)-N,N-dimethylanilineHCID 2724699PyBOPHCID 575806954-[5-(1-Oxo-2,3-dihydro-1H-isoindol-5-yl)-imidazo[1,2-a]pyridin-8-ylamino]-benzoic acid

Produkt 1

HCID 249896475-(8-(4-(1,4'-Bipiperidine-1'-carbonyl)phenylamino)imidazo[1,2-a]pyridin-5-yl)isoindolin-1-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 4-[5-(1-oxo-2,3-dihydro-1H-isoindol-5-yl)-imidazo[1,2-a]pyridin-8-ylamino]-benzoic acid (37.0 mg, 0.096 mmol), 4-dimethylaminobenzylamine (15.91 mg, 0.106 mmol) and triethylamine (10.72 mg, 0.047 mL, 0.106 mmol) in dimethylformamide (0.4 mL) under nitrogen is added benzotriazole-1-yl-oxy-tris-pyrrolidino-phosphonium hexafluorophosphate (55.10 mg, 0.106 mmol). The reaction mixture is then stirred at room temperature for 18 hours. The mixture is then diluted with EtOAc and washed with saturated aqueous NaHCO3. The combined organic layers are dried (MgSO4) and the solvent is removed under reduced. The crude product is purified by reverse phase HPLC to yield the title compound.

Aufarbeitung

  1. washwashed with saturated aqueous NaHCO3
  2. dry with materialThe combined organic layers are dried (MgSO4)
  3. customthe solvent is removed
  4. customThe crude product is purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-dc7734a89d844ac084dc0fa1c71483da
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07951818B2

Notizen zur Reaktion

Wird geladen…