Potassium Acetate → HCID 67975389, compound

HRID 1424495Notes

Reaction equation

HRID 1424495 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]=[C:9]([CH2:18][N:19]3[C:23]4[CH:24]=[N:25][CH:26]=[CH:27][C:22]=4[N:21]([CH:28]4[CH2:30][CH2:29]4)[C:20]3=[O:31])[N:10]([CH2:11][CH2:12][CH2:13][C:14]([F:17])([F:16])[F:15])[C:5]2=[CH:4][CH:3]=1.CC([O-])=O.[K+]>CO.[Pd]>[CH:28]1([N:21]2[C:22]3[CH:27]=[CH:26][N:25]=[CH:24][C:23]=3[N:19]([CH2:18][C:9]3[N:10]([CH2:11][CH2:12][CH2:13][C:14]([F:15])([F:17])[F:16])[C:5]4[C:6]([N:8]=3)=[N:7][CH:2]=[CH:3][CH:4]=4)[C:20]2=[O:31])[CH2:30][CH2:29]1

Participants

5

Reactant 2

HCID 517044Potassium AcetateHCID 86698151HCID 86698151, compound

Product 1

HCID 67975389HCID 67975389, compoundYield 59.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Compound 39 (1000 mg, 2.22 mmol) was dissolved in 30 mL MeOH. Pd/C (10%) and KOAc (218 mg, 2.22 mol) were added. The mixture was placed under H2 and hydrogenated overnight. The mixture was filtrated over a plug of dicalite and evaporated. Compound 41 was purified by column chromatography on silicagel using CH2Cl2 to CH2Cl2/MeOH(NH3) 9-1 as the eluent. After evaporation 550 mg (59% yield) of 41 was obtained as a white solid with a purity of 99%. m/z=417 (M+H)+. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.93-1.05 (m, 2H), 1.18 (s, 2H), 1.91 (s, 2H), 2.12-2.31 (m, 2H), 2.91 (tt, J=6.93, 3.48 Hz, 1H), 4.46 (t, J=7.80 Hz, 2H), 5.42 (s, 2H), 7.14 (d, J=5.27 Hz, 1H), 7.25 (dd, J=8.28, 4.77 Hz, 1H), 7.66 (dd, J=8.16, 1.38 Hz, 1H), 8.36 (d, J=5.27 Hz, 1H), 8.59 (dd, J=4.77, 1.51 Hz, 1H), 8.80 (s, 1H).

Workup

  1. filtrationThe mixture was filtrated over a plug of dicalite
  2. customevaporated
  3. customCompound 41 was purified by column chromatography on silicagel

Sources & evidence

ORD record
ord-3a0aeb9b590d43b196959ed9322ec2c0
Source dataset
uspto-grants-2015_01
Patent number
US08927720B2

Reaction notes

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