Sodium Carbonate → (4-Imidazol-1-yl-phenyl)-[5-(1H-pyrazol-4-yl)-imidazo[1,2-a]pyrazin-8-yl]-amine

HRID 1366166

Reaction equation

HRID 1366166 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[CH:22]=[CH:21][N:20]=[CH:19]3)=[CH:14][CH:13]=2)=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:31]2[CH:32]=[N:33][NH:34][CH:35]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>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.CN(C=O)C.O1CCOCC1>[NH3:4].[N:18]1([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:31]4[CH:32]=[N:33][NH:34][CH:35]=4)=[CH:3][N:4]=3)=[CH:13][CH:14]=2)[CH:22]=[CH:21][N:20]=[CH:19]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 59023113(5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(4-imidazol-1-yl-phenyl)-amine

Product 2

HCID 222AmmoniaHCID 59023138(4-Imidazol-1-yl-phenyl)-[5-(1H-pyrazol-4-yl)-imidazo[1,2-a]pyrazin-8-yl]-amineYield 110.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 217120691,4-dioxane N,N-dimethylformamideSolvent

Procedure

In the same way as described for Compound 178, step 4, using (5-bromo-imidazo[1,2-a]pyrazin-8-yl)-(4-imidazol-1-yl-phenyl)-amine (49.8 mg, 0.14 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (54.4 mg, 0.280 mmol), Pd(PPh3)4 (39.1 mg, 0.0338 mmol) and 1.5 M Na2CO3 (0.748 mL, 1.12 mmol) in 2:1 DMF-dioxane (1.5 mL). Purification by Isolute Flash SiII cartridge chromatography eluting with 98:2 DCM:NH3 (7M in MeOH), followed by 97:3 DCM:NH3 (7M in MeOH) and 95:5 DCM:NH3 (7M in MeOH) affords the title compound as a white solid (26.5 mg, 55%). LCMS: Rt 1.75 min (96%), m/z (APCI) 343 (M+H)+; 1H-NMR (400 MHz, d6-DMSO) δ (ppm) 7.13 (1H, s), 7.63 (2H, d), 7.67 (1H, s), 7.73 (1H, s), 7.79 (1H, s), 8.09 (1H, br s), 8.18 (1H, s), 8.22 (1H, s), 8.27 (2H, d), 8.43 (1H, br s), 9.82 (1H, s), 13.39 (1H, br s).

Workup

  1. customPurification by Isolute Flash SiII cartridge chromatography
  2. washeluting with 98:2 DCM

Sources & evidence

ORD record
ord-23dbbad8a3814b8ead35c74d7359edc4
Source dataset
uspto-grants-2011_02
Patent number
US07893058B2

Linked notes

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