Potassium Carbonate → HCID 68441564, compound

HRID 1805982Notes

Reaction equation

HRID 1805982 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([C:14]3[N:15]=[C:16](CCCN)[C:17]4[S:22][CH2:21][CH2:20][C:18]=4[N:19]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:27]([NH2:35])(=[O:34])[C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+].C[N:43](C)[C@@H:44]1CCC[CH2:46][C@H:45]1N>[Cu](I)I.O1CCOCC1>[CH2:44]([NH:43][C:16]1[C:17]2[S:22][CH2:21][CH2:20][C:18]=2[N:19]=[C:14]([N:11]2[CH2:12][CH2:13][N:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:35][C:27](=[O:34])[C:28]4[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=4)=[CH:3][CH:4]=3)[CH2:9][CH2:10]2)[N:15]=1)[CH2:45][CH3:46]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 15074IsonicotinamideHCID 11275066(1R,2R)-N1,N1-Dimethylcyclohexane-1,2-diamineHCID 86616267HCID 86616267, compound

Product 1

HCID 68441564HCID 68441564, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

0.170 g (0.4 mmol) of {2-[4-(4-iodophenyl)piperazin-1-yl]-6,7-dihydrothieno[3,2-d]pyrimidin-4-yl}propylamine (VIII), 0.054 g (0.4 mmol) of isonicotinamide, 0.100 g (0.7 mmol) of potassium carbonate, and 0.004 g is (0.02 mmol) of copper iodide are taken, and under an argon atmosphere 1 mL of anhydrous/degassed dioxane and 0.006 mL (0.04 mmol) of trans-N,N-dimethyl-1,2-cyclohexanediamine are added. The reaction mixture is reacted for 2 hours at 140° C. in the microwave, then filtered through silica gel with petroleum ether/ethyl acetate (1/1) and then ethyl acetate/methanol (8/2), and concentrated by evaporation. The residue is purified by chromatography (column: Microsorb, RP-C18, 300 Å, 10 μm, 21.4*250 mm, eluant: acetonitrile+0.1% formic acid (A), water+0.13% formic acid (B)).

Workup

  1. customThe reaction mixture is reacted for 2 hours at 140° C. in the microwave
  2. filtrationfiltered through silica gel with petroleum ether/ethyl acetate (1/1)
  3. concentrationethyl acetate/methanol (8/2), and concentrated by evaporation
  4. customThe residue is purified by chromatography (column: Microsorb, RP-C18, 300 Å, 10 μm, 21.4*250 mm, eluant: acetonitrile+0.1% formic acid (A), water+0.13% formic acid (B))

Sources & evidence

ORD record
ord-a2b0ff04137d440a96d2f5cc353220d5
Source dataset
uspto-grants-2013_01
Patent number
US08354531B2

Reaction notes

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