Cesium carbonate → HCID 24781340, compound

HRID 1024648Notes

Reaction equation

HRID 1024648 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16](=[O:17])[C:15]3[N:14]=[CH:13][N:12]([C:18]4[CH:19]=[C:20]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH:21]=[CH:22][CH:23]=4)[C:11]=3[N:10]=[C:9]2[C:29]2[CH:34]=[CH:33][C:32](B3OC(C)(C)C(C)(C)O3)=[CH:31][CH:30]=2)=[CH:4][CH:3]=1.I[N:45]1[CH:50]=[CH:49][CH:48]=[CH:47][NH:46]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16](=[O:17])[C:15]3[N:14]=[CH:13][N:12]([C:18]4[CH:19]=[C:20]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])[CH:21]=[CH:22][CH:23]=4)[C:11]=3[N:10]=[C:9]2[C:29]2[CH:34]=[CH:33][C:32]([C:50]3[N:45]=[N:46][CH:47]=[CH:48][CH:49]=3)=[CH:31][CH:30]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 57899376HCID 57899376, compoundHCID 86634838HCID 86634838, compound

Product 1

HCID 24781340HCID 24781340, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of N-(3-{1-(4-chloro-phenyl)-6-oxo-2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-1,6-dihydro-purin-9-yl}-phenyl)-methanesulfonamide (prepared as described in example 26, 0.500 g, 0.809 mmol) in N,N-dimethylformamide (20 mL) is degassed with argon for 0.5 h. Then 2-iodopyridazine (0.250 g, 1.21 mmol), cesium carbonate (0.527 g, 1.61 mmol), Pd(dppf)2Cl2 (0.059 g, 0.08 mmol) is added and the resulted mixture is degassed with argon for 0.5 h. The reaction mixture is heated to reflux for 3 h. The reaction mixture is poured into with water and extracted with ethyl acetate (3×). The combined organic layer is washed with brine, dried over Na2SO4, concentrated, and purified by column chromatography to afford N-{3-[1-(4-chloro-phenyl)-6-oxo-2-(4-pyridazin-3-yl-phenyl)-1,6-dihydro-purin-9-yl]-phenyl}-methane sulfonamide. 1H NMR (DMSO-d6, 400 MHz) δ 10.2 (br, 1H), 9.20 (m, 1H), 8.62 (m, 1H), 8.21 (d, 1H), 8.06 (m, 2H), 7.77 (m, 2H), 7.42-7.57 (m, 8H), 7.25 (d, 1H), 3.05 (s, 3H); LC-MS calculated for C28H20ClN7O3S (M+H+) 570.1, found 570.0.

Workup

  1. customthe resulted mixture is degassed with argon for 0.5 h
  2. temperatureThe reaction mixture is heated
  3. temperatureto reflux for 3 h
  4. additionThe reaction mixture is poured into with water
  5. extractionextracted with ethyl acetate (3×)
  6. washThe combined organic layer is washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. custompurified by column chromatography

Sources & evidence

ORD record
ord-a7ddcda650ec4ba099e432d9878796dc
Source dataset
uspto-grants-2014_05
Patent number
US08722691B2

Reaction notes

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