Acetic Acid → HCID 58094826, compound

HRID 2282334Notes

Reaction equation

HRID 2282334 reaction equation
C([N:4]1[CH:8]=[CH:7][N:6]=[C:5]1[C:9]1[S:13][C:12]([C:14]2[C:15]3[N:22]=[C:21]([NH2:23])[S:20][C:16]=3[N:17]=[CH:18][N:19]=2)=[CH:11][C:10]=1[C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=1[Cl:31])C=C.C(O)(=O)C.C1([SiH3])C=CC=CC=1.C([O-])(O)=O.[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.C(Cl)Cl>[Cl:31][C:25]1[CH:26]=[C:27]([Cl:30])[CH:28]=[CH:29][C:24]=1[C:10]1[CH:11]=[C:12]([C:14]2[C:15]3[N:22]=[C:21]([NH2:23])[S:20][C:16]=3[N:17]=[CH:18][N:19]=2)[S:13][C:9]=1[C:5]1[NH:6][CH:7]=[CH:8][N:4]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 12752PhenylsilaneHCID 516892Sodium BicarbonateHCID 58095014HCID 58095014, compound

Product 1

HCID 58094826HCID 58094826, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

A mixture of 7-[5-(1-allyl-1H-imidazol-2-yl)-4-(2,4-dichlorophenyl)-2-thienyl][1,3]thiazolo[5,4-d]pyrimidin-2-amine (28.0 mg, 0.058 mmol), acetic acid (2.0 mL) and DCM (6.0 mL) was degassed with vacuum and then the atmosphere was replaced with nitrogen. To the mixture, were added tetrakis(triphenylphosphine)palladium(0) (7.03 mg, 0.00608 mmol) and phenylsilane (0.10 mL, 0.81 mmol). The resulting mixture was stirred at 40° C. for 30 min. The mixture was allowed to cool to rt followed by adding sat. NaHCO3 and DCM. After being stirred for 10 min, the organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Column chromatography was performed to yield the title compound (15.1 mg, 59%) as a pale yellow solid. LCMS: (AA) ES+445, 447. 1H NMR (400 MHz, d6-DMSO) δ: 11.82 (bs, 1H), 8.64 (s, 1H), 8.39-8.37 (m, 2H), 7.73 (d, J=2.0 Hz, 1H), 7.64-7.42 (m, 3H), 7.12 (bs, 1H), 6.95 (bs, 1H).

Workup

  1. customwas degassed with vacuum
  2. temperatureto cool to rt
  3. stirringAfter being stirred for 10 min
  4. washthe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f4bb6bd53f8e4b18af526b5cdff512b5
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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