Sodium Carbonate → HCID 67047599, compound

HRID 605975Notes

Reaction equation

HRID 605975 reaction equation
CN1CCN(C2C=CC(NC3C4N(N=CN=4)C(C4C=C(C(N)=O)SC=4)=CN=3)=CC=2)CC1.[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][N:42]([C:45]2[CH:50]=[CH:49][C:48]([NH:51][C:52]3[C:53]4[N:54]([N:59]=[CH:60][N:61]=4)[C:55](Br)=[CH:56][N:57]=3)=[CH:47][CH:46]=2)[C:41](=[O:62])[CH2:40]1)=[O:38])([CH3:35])([CH3:34])[CH3:33].CC1(C)C(C)(C)OB([C:71]2[CH:72]=[C:73]3[C:77](=[CH:78][CH:79]=2)[C:76](=[O:80])[NH:75][CH2:74]3)O1.C([O-])([O-])=O.[Na+].[Na+]>[Cl-].[Na+].O.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.C1(C)C=CC=CC=1.O1CCOCC1>[C:32]([O:36][C:37]([N:39]1[CH2:44][CH2:43][N:42]([C:45]2[CH:50]=[CH:49][C:48]([NH:51][C:52]3[C:53]4[N:54]([N:59]=[CH:60][N:61]=4)[C:55]([C:71]4[CH:72]=[C:73]5[C:77](=[CH:78][CH:79]=4)[C:76](=[O:80])[NH:75][CH2:74]5)=[CH:56][N:57]=3)=[CH:47][CH:46]=2)[C:41](=[O:62])[CH2:40]1)=[O:38])([CH3:35])([CH3:34])[CH3:33]

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 219557955-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-oneHCID 575899284-{8-[4-(4-Methyl-piperazin-1-yl)-phenylamino]-[1,2,4]triazolo[1,5-a]pyrazin-5-yl}-thiophene-2-carboxylic acid amideHCID 866196644-[4-(5-Bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-phenyl]-3-oxo-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 67047599HCID 67047599, compoundYield 47%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolventHCID 312751,4-DioxaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

This compound may be prepared using methods as described for Compound 6, step 4, using 4-[4-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-phenyl]-3-oxo-piperazine-1-carboxylic acid tert-butyl ester (115 mg, 0.24 mmol), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-isoindol-1-one (92 mg, 0.35 mmol), and Pd(PPh3)4 (83 mg, 0.072 mmol) in 1.5M Na2CO3 (aq) (1.3 mL, 1.92 mmol), and dioxane (2.5 mL). The reaction mixture is diluted with brine then toluene is added and a precipitate is formed and collected by filtration. The resultant solid is dissolved in DCM and filtered through a silica cartridge to afford the title compound as a yellow solid (60 mg, 47%).

Workup

  1. customThis compound may be prepared
  2. customa precipitate is formed
  3. filtrationcollected by filtration
  4. dissolutionThe resultant solid is dissolved in DCM
  5. filtrationfiltered through a silica cartridge

Sources & evidence

ORD record
ord-51d75768b34a416a811d709fcd73ba6b
Source dataset
uspto-grants-2011_03
Patent number
US07915256B2

Reaction notes

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