(5-Bromoimidazo[1,2-a]pyrazin-8-yl)-(4-(4-methylpiperazin-1-yl)phenyl)amine → HCID 59023013, compound

HRID 1366138Notes

Reaction equation

HRID 1366138 reaction equation
Br[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N:18]3[CH2:23][CH2:22][N:21]([CH3:24])[CH2:20][CH2:19]3)=[CH:14][CH:13]=2)=[N:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:30]1[CH:31]=[CH:32][C:33]([C:36]([NH2:38])=[O:37])=[N:34][CH:35]=1)CCC>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH3:4].[CH3:24][N:21]1[CH2:22][CH2:23][N:18]([C:15]2[CH:16]=[CH:17][C:12]([NH:11][C:5]3[C:6]4[N:7]([CH:8]=[CH:9][N:10]=4)[C:2]([C:30]4[CH:31]=[CH:32][C:33]([C:36]([NH2:38])=[O:37])=[N:34][CH:35]=4)=[CH:3][N:4]=3)=[CH:13][CH:14]=2)[CH2:19][CH2:20]1

Participants

6

Reactant 2

HCID 59022979(5-Bromoimidazo[1,2-a]pyrazin-8-yl)-(4-(4-methylpiperazin-1-yl)phenyl)amineHCID 590230495-(Tributylstannyl)-2-pyridinecarboxamide

Product 2

HCID 222AmmoniaHCID 59023013HCID 59023013, compoundYield 3%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A degassed mixture of (5-bromoimidazo[1,2-a]pyrazin-8-yl)-(4-(4-methylpiperazin-1-yl)phenyl)amine (59 mg, 0.154 mol), 5-tributylstannanyl-pyridine-2-carboxylic acid amide (0.127, 0.309 mmol), PdCl2(PPh3)2 (0.027 g, 0.038 mmol) in DMF (2 mL), is stirred at 85° C. for 20 hours. The reaction mixture is partitioned between EtOAc and water. The organic layer is washed with water (4×), dried over MgSO4, filtered and concentrated in vacuo. The crude is purified by silica gel column chromatography eluting with DCM followed by 97:3 DCM:NH3 (7M in MeOH) affording the title compound (2.0 mg, 3%). LCMS: Rt 1.75 min (92%) m/z (APCI) 429 (M+H)+; 1H-NMR (400 MHz, d6-DMSO) δ (ppm) 2.26 (3H, s), 2.49-2.51 (4H, t), 3.12-3.15 (4H, m), 6.97 (2H, d), 7.62 (1H, s), 7.73 (1H, s), 7.77 (1H, br s), 7.91 (2H, d), 8.08 (1H, s), 8.22 (1H, d), 8.24 (1H, br s), 8.37-8.40 (1H, m), 8.96 (1H, s), 9.61 (1H, s).

Workup

  1. customThe reaction mixture is partitioned between EtOAc and water
  2. washThe organic layer is washed with water (4×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude is purified by silica gel column chromatography
  7. washeluting with DCM

Sources & evidence

ORD record
ord-0f2298011f074a84b28b4f007d279feb
Source dataset
uspto-grants-2011_02
Patent number
US07893058B2

Reaction notes

Loading…