Sodium Carbonate → HCID 59023001, compound

HRID 1921828Notes

Reaction equation

HRID 1921828 reaction equation
[N:1]1(C2C=CC(NC3C4N(C=CN=4)C(C4C=C5C(=CC=4)C(=O)NC5)=CN=3)=CC=2)CCOCC1.Br[C:34]1[N:39]2[CH:40]=[CH:41][N:42]=[C:38]2[C:37]([NH:43][C:44]2[CH:49]=[CH:48][C:47]([N:50]3[CH2:55][CH2:54][N:53]([CH:56]([CH3:58])[CH3:57])[CH2:52][CH2:51]3)=[CH:46][CH:45]=2)=[N:36][CH:35]=1.CC1(C)C(C)(C)OB([C:67]2[CH:68]=[C:69]([C:72]([NH2:74])=[O:73])[O:70][CH:71]=2)O1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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>[NH3:1].[CH:56]([N:53]1[CH2:54][CH2:55][N:50]([C:47]2[CH:48]=[CH:49][C:44]([NH:43][C:37]3[C:38]4[N:39]([CH:40]=[CH:41][N:42]=4)[C:34]([C:67]4[CH:68]=[C:69]([C:72]([NH2:74])=[O:73])[O:70][CH:71]=4)=[CH:35][N:36]=3)=[CH:45][CH:46]=2)[CH2:51][CH2:52]1)([CH3:58])[CH3:57]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 573939935-[8-(4-Morpholin-4-yl-phenylamino)-imidazo[1,2-a]pyrazin-5-yl]-2,3-dihydro-isoindol-1-oneHCID 575899904-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carboxamideHCID 59022995(5-Bromo-imidazo[1,2-a]pyrazin-8-yl)-[4-(4-isopropyl-piperazin-1-yl)-phenyl]-amine

Product 2

HCID 222AmmoniaHCID 59023001HCID 59023001, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

In the same way as described for Compound 178, step 4, using, 5-bromo-imidazo[1,2-a]pyrazin-8-yl-[4-(4-isopropyl-piperazin-1-yl)-phenyl]-amine (0.08 g, 0.19 mmol), 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-furan-2-carboxylic acid amide (0.092 g, 0.39 mmol), 1.5M Na2CO3 (1.02 mL, 1.53 mmol) and Pd(PPh3)4 (0.055 g, 0.47 mmol) in dioxane (4 mL). Purification using silica gel column chromatography, eluting with DCM followed by 97:3 DCM:NH3 (7M in MeOH), affords the title compound (30.2 mg, 36%).

Workup

  1. customPurification
  2. washeluting with DCM

Sources & evidence

ORD record
ord-51372f03edf7471dbfb5defc0310329e
Source dataset
uspto-grants-2012_05
Patent number
US08173656B2

Reaction notes

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