Sodium Carbonate → HCID 44225402, compound

HRID 880524Notes

Reaction equation

HRID 880524 reaction equation
IC1C2C(=NC=NC=2N)N(C(C)C)N=1.[CH:15]1([N:20]2[C:24]3=[N:25][CH:26]=[N:27][C:28]([NH2:29])=[C:23]3[C:22](I)=[N:21]2)[CH2:19][CH2:18][CH2:17][CH2:16]1.CC1(C)C(C)(C)OB([C:39]2[CH:51]=[CH:50][C:42]3[N:43]=[C:44]([NH:46][C:47](=[O:49])[CH3:48])[S:45][C:41]=3[CH:40]=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]>[NH2:29][C:28]1[N:27]=[CH:26][N:25]=[C:24]2[N:20]([CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[N:21]=[C:22]([C:39]3[CH:51]=[CH:50][C:42]4[N:43]=[C:44]([NH:46][C:47](=[O:49])[CH3:48])[S:45][C:41]=4[CH:40]=3)[C:23]=12

Participants

10

Reactant 5

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 223468081-cyclopentyl-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-amineHCID 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 44225402HCID 44225402, compoundYield 35.9%

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 (601 (1.21 g, 3.68 mmol), N-(6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)acetamide (I-5) (1.18 g, 3.71 mmol), Pd(OAc)2 (0.17 g, 0.75 mmol), triphenyl phosphine (0.59 g, 2.22 mmol) and Na2CO3 (1.98 g, 18.6 mmol) was dissolved in a mixture of DMF (3 mL), EtOH (1.5 mL) and H2O (1.5 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 flash column chromatography on silica gel (200-300 mesh) eluting with DCM/MeOH (20/1) to give the desired product, N-(6-(4-amino-1-cyclopentyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)benzo[d]thiazol-2-yl)acetamide (602) (0.52 g, 35.9%) as an off-white solid. ESI-MS (M+H)+ m/z: 394.1.

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 flash column chromatography on silica gel (200-300 mesh)
  7. washeluting with DCM/MeOH (20/1)

Sources & evidence

ORD record
ord-8826108848c541a5b4d3bd383a2f142e
Source dataset
uspto-grants-2015_03
Patent number
US08993580B2

Reaction notes

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