Sodium Iodide → N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-(4-pyridinylethynyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

HRID 1522372

Reaktionsgleichung

Reaktionsgleichung von HRID 1522372
Cl[C:2]1[CH:3]=[C:4]([C:14]([NH:16][CH2:17][C:18]2[C:19](=[O:26])[NH:20][C:21]([CH3:25])=[CH:22][C:23]=2[CH3:24])=[O:15])[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=1.[I-].[Na+].C(N(CC)CC)C.[CH2:36]1[CH2:46]C[N:44]2[C:39](=NC[CH2:42][CH2:43]2)[CH2:38][CH2:37]1.C(C1C=CN=CC=1)#C>[Zn].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CS(C)=O>[CH3:24][C:23]1[CH:22]=[C:21]([CH3:25])[NH:20][C:19](=[O:26])[C:18]=1[CH2:17][NH:16][C:14]([C:4]1[C:5]2[CH:10]=[N:9][N:8]([CH:11]([CH3:13])[CH3:12])[C:6]=2[N:7]=[C:2]([C:46]#[C:36][C:37]2[CH:38]=[CH:39][N:44]=[CH:43][CH:42]=2)[CH:3]=1)=[O:15]

Komponenten

9

Edukt 5

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 6428014-EthynylpyridineHCID 565974256-Chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Produkt 1

HCID 56597871N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-6-(4-pyridinylethynyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 178418397HCID 178418397, VerbindungKatalysatorHCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

The title compound was prepared in the same manner as described in example 31 from 6-chloro-N-[(4,6-dimethyl-2-oxo-1,2-dihydro-3-pyridinyl)methyl]-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxamide (0.15 g, 0.401 mmol), sodium iodide (0.012 g, 0.080 mmol), zinc (5.25 mg, 0.080 mmol), DMSO (4.0 mL), triethylamine (0.168 mL, 1.204 mmol), DBU (0.121 mL, 0.802), 4-ethynylpyridine (0.112 g, 0.802 mmol), and Pd(Ph3P)4 (0.046 g, 0.040 mmol). The crude product was purified by silica gel chromatography (eluent: Gradient of 5-100% of DCM and chloroform containing 10% 2M Ammonia (in methanol)). The isolated product was dried in vacuum oven for 18 hr. to afford the final product as 0.032 g (18%). LCMS E-S (M+H)=441.1. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.51 (d, J=6.57 Hz, 6 H), 2.13 (s, 3 H), 2.21 (s, 3 H), 4.37 (d, J=4.80 Hz, 2 H), 5.20-5.32 (m, 1 H), 5.90 (s, 1 H), 7.62-7.69 (m, 2 H), 7.93 (s, 1 H), 8.45 (s, 1 H), 8.67-8.75 (m, 2 H), 8.93 (t, J=4.80 Hz, 1 H), 11.55 (s, 1 H).

Aufarbeitung

  1. customThe title compound was prepared in the same manner
  2. customThe crude product was purified by silica gel chromatography (eluent: Gradient of 5-100% of DCM and chloroform containing 10% 2M Ammonia (in methanol))
  3. customThe isolated product was dried in vacuum oven for 18 hr

Quellen und Nachweise

ORD-Eintrag
ord-5e83ab2c913f458c9002704c89869124
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073924B2

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