Sodium Carbonate → HCID 44203864, compound

HRID 880523Notes

Reaction equation

HRID 880523 reaction equation
I[C:2]1[C:10]2[C:5](=[N:6][CH:7]=[N:8][C:9]=2[NH2:11])[N:4]([CH:12]([CH3:14])[CH3:13])[N:3]=1.CC1(C)C(C)(C)OB([C:23]2[CH:35]=[CH:34][C:26]3[N:27]=[C:28]([NH:30][C:31](=[O:33])[CH3:32])[S:29][C:25]=3[CH:24]=2)O1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.CCO.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[NH2:11][C:9]1[N:8]=[CH:7][N:6]=[C:5]2[N:4]([CH:12]([CH3:14])[CH3:13])[N:3]=[C:2]([C:23]3[CH:35]=[CH:34][C:26]4[N:27]=[C:28]([NH:30][C:31](=[O:33])[CH3:32])[S:29][C:25]=4[CH:24]=3)[C:10]=12

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 249053373-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amineHCID 51354026n-(6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamide

Product 1

HCID 44203864HCID 44203864, compoundYield 48.3%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3-iodo-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (104) (1.88 g, 6.2 mmol), N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamide (I-5) (2.0 g, 6.3 mmol), Pd(OAc)2 (0.28 g, 1.24 mmol), triphenyl phosphine (0.98 g, 3.7 mmol) and Na2CO3 (3.3 g, 31 mmol) was dissolved in a mixture of DMF (5 mL), EtOH (2 mL) and H2O (2 mL). The resulting mixture was degassed and back-filled with argon three times and then stirred at 80° C. for 4 h. The mixture was allowed to cool to room temperature and filtered. The filtrate was concentrated in vacuo. The crude product was purified by chromatography eluting with DCM/MeOH (20/1) on a silica gel column (200-300 mesh) to afford the desired product N-(6-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)benzo[d]thiazol-2-yl)acetamide (501) (1.1 g, 48.2%) as a white solid. ESI-MS (M+H)+ m/z: 368.4.

Workup

  1. customThe resulting mixture was degassed
  2. additionback-filled with argon three times
  3. temperatureto cool to room temperature
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customThe crude product was purified by chromatography
  7. washeluting with DCM/MeOH (20/1) on a silica gel column (200-300 mesh)

Sources & evidence

ORD record
ord-ae0a20d4163345469ced54130a8b87bb
Source dataset
uspto-grants-2015_03
Patent number
US08993580B2

Reaction notes

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