Potassium Iodide → HCID 178435022, compound

HRID 2294837Notes

Reaction equation

HRID 2294837 reaction equation
C([N:4]1[CH2:9][CH2:8][C:7]2[C:10]([CH2:14][CH2:15]Br)=[C:11]([CH3:13])[S:12][C:6]=2[CH2:5]1)(=[O:3])C.Cl.[F:18][C:19]1[CH:27]=[C:26]2[C:22]([C:23]([CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[N:24][NH:25]2)=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CN(C)C=O.C1(C)C=CC=CC=1>[OH2:3].[F:18][C:19]1[CH:27]=[C:26]2[C:22]([C:23]([CH:28]3[CH2:33][CH2:32][N:31]([CH2:15][CH2:14][C:10]4[C:7]5[CH2:8][CH2:9][NH:4][CH2:5][C:6]=5[S:12][C:11]=4[CH3:13])[CH2:30][CH2:29]3)=[N:24][NH:25]2)=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 214719356-Acety-3-(2-bromoethyl)-4,5,6,7-tetrahydro-2-methylthieno[2,3-c]pyridineHCID 178478941HCID 178478941, compound

Product 1

HCID 178435022HCID 178435022, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 514 mg of 6-acety-3-(2-bromoethyl)-4,5,6,7-tetrahydro-2-methylthieno[2,3-c]pyridine, 511 mg of 4-(6-fluoro-1H-indazol-3-yl)piperidine hydrochloride, 690 mg of potassium carbonate and 365 mg of potassium iodide in 10 ml of dimethylformamide and 10 ml of toluene was stirred at 90° C. for 22 hours and concentrated in vacuo. To the residue were added ethyl acetate and water, and separated. The ethyl acetate layer was washed with water, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on a silica gel and recrystallized from the mixture of diisopropyl ether and isopropyl alcohol to give 170 mg of 6-acetyl-3-(2-(4-(6-fluoro-1H-indazol-3-yl)piperidin-1-yl)ethyl-4,5,6,7-tetrahydro-2-methylthieno[2,3-c]pyridine monohydrate, m.p. 116°-119° C.

Workup

  1. concentrationconcentrated in vacuo
  2. additionTo the residue were added ethyl acetate and water
  3. customseparated
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography on a silica gel
  8. customrecrystallized from the mixture of diisopropyl ether and isopropyl alcohol

Sources & evidence

ORD record
ord-c7849edc58a3441c83dcd34d32450725
Source dataset
uspto-grants-1997_11
Patent number
US05691330

Reaction notes

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