Acetic Acid → HCID 58094809, compound

HRID 2282333Notes

Reaction equation

HRID 2282333 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]([NH:23][C:24](=[O:26])[CH3:25])[S:20][C:16]=3[N:17]=[CH:18][N:19]=2)=[CH:11][C:10]=1[C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=1[Cl:34])C=C.C(O)(=O)C.C1([SiH3])C=CC=CC=1>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.O>[Cl:34][C:28]1[CH:29]=[C:30]([Cl:33])[CH:31]=[CH:32][C:27]=1[C:10]1[CH:11]=[C:12]([C:14]2[C:15]3[N:22]=[C:21]([NH:23][C:24](=[O:26])[CH3:25])[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 3

HCID 176Acetic AcidHCID 12752PhenylsilaneHCID 58094900HCID 58094900, compound

Product 1

HCID 58094809HCID 58094809, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
40 °C

Procedure

A mixture of N-{7-[5-(1-allyl-1H-imidazol-2-yl)-4-(2,4-dichlorophenyl)-2-thienyl][1,3]thiazolo[5,4-d]pyrimidin-2-yl}acetamide (200.0 mg, 0.3792 mmol), acetic acid (5 mL, 90 mmol) and DCM (25 mL) was degassed with vacuum and then the atmosphere was replaced with nitrogen. To the mixture, tetrakis(triphenylphosphine)palladium(0) (10.7 mg, 0.00923 mmol) and phenylsilane (0.187 mL, 1.517 mmol) were added. The resulting mixture was stirred at 40° C. for 30 min. The mixture was allowed to cool to rt followed by adding water and DCM. After being stirred for 10 min, the organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. Column chromatography was performed to yield the title compound (57.3 mg, 31%) as a pale yellow solid. LCMS: (AA) ES+ 487, 489. 1H NMR (400 MHz, d6-DMSO) δ: 12.74 (bs, 1H), 11.88 (bs, 1H), 8.95 (s, 1H), 8.52 (s, 1H), 7.77 (d, J=2.3 Hz, 1H), 7.53-7.45 (m, 2H), 7.16 (bs, 1H), 6.98 (bs, 1H), 2.24 (s, 3H).

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 magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa4eec51bc48466cac8730315431a26f
Source dataset
uspto-grants-2015_09
Patent number
US09139589B2

Reaction notes

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