Sodium Carbonate → 5-{8-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-imidazo[1,2-a]pyrazin-5-yl}-nicotinamide

HRID 1366133Notes

Reaction equation

HRID 1366133 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[N:11][CH:12]=[C:13]([CH:17]=2)[C:14]([NH2:16])=[O:15])O1.Br[C:20]1[N:25]2[CH:26]=[CH:27][N:28]=[C:24]2[C:23]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([N:36]3[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]3)=[CH:32][CH:31]=2)=[N:22][CH:21]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.CN(C=O)C.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>[NH3:11].[CH3:42][N:39]1[CH2:40][CH2:41][N:36]([C:33]2[CH:34]=[CH:35][C:30]([NH:29][C:23]3[C:24]4[N:25]([CH:26]=[CH:27][N:28]=4)[C:20]([C:9]4[CH:10]=[N:11][CH:12]=[C:13]([CH:17]=4)[C:14]([NH2:16])=[O:15])=[CH:21][N:22]=3)=[CH:31][CH:32]=2)[CH2:37][CH2:38]1

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 59022979(5-Bromoimidazo[1,2-a]pyrazin-8-yl)-(4-(4-methylpiperazin-1-yl)phenyl)amineHCID 590231175-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carboxamide

Product 2

HCID 222AmmoniaHCID 590230555-{8-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-imidazo[1,2-a]pyrazin-5-yl}-nicotinamideYield 11%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Procedure

In the same way as described for Compound 127, step 4, using 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-nicotinamide (51.6 mg, 0.207 mmol), (5-bromoimidazo[1,2-a]pyrazin-8-yl)-(4-(4-methylpiperazin-1-yl)phenyl)amine (40 mg, 0.103 mol), Pd(PPh3)4 (30 mg, 0.026 mmol) and 1.5M Na2CO3 (0.55 mL), in dioxane (0.46 mL) and DMF (1.01 mL). The residue is chromatographed on silica gel, eluting with DCM followed by 96:4 DCM:NH3 (7M in MeOH) to afford the title compound (4.8 mg, 11%). LCMS: Rt 1.74 min (97%) m/z (APCI) 429; 1H-NMR (400 MHz, d6-DMSO) δ (ppm).2.26 (3H, s), 2.49-2.54 (4H, m), 3.12 (4H, m), 6.97 (2H, d), 7.57 (1H, s), 7.73 (1H, s), 7.75 (1H, br s), 7.91 (2H, d), 8.07 (1H, s), 8.29 (1H, br s), 8.54 (1H, s), 9.03 (1H, s), 9.14 (1H, s), 9.58 (1H, s).

Workup

  1. customThe residue is chromatographed on silica gel
  2. washeluting with DCM

Sources & evidence

ORD record
ord-6c64ff5a276948fbb35d02816ad6357c
Source dataset
uspto-grants-2011_02
Patent number
US07893058B2

Reaction notes

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