Potassium Carbonate → HCID 18446524, compound

HRID 1868295Notes

Reaction equation

HRID 1868295 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:8])=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].Cl[C:18]1[C:23]2[CH:24]=[C:25]([I:27])[S:26][C:22]=2[C:21]([C:28]#[N:29])=[CH:20][N:19]=1>CN1C(=O)CCC1>[I:27][C:25]1[S:26][C:22]2[C:21]([C:28]#[N:29])=[CH:20][N:19]=[C:18]([NH:8][CH2:7][C:6]3[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C:23]=2[CH:24]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 754524-MethoxybenzylamineHCID 18446569HCID 18446569, compound

Product 1

HCID 18446524HCID 18446524, compoundYield 78.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

To NMP (41.3 mL) and 4-methoxybenzylamine (3.66 mL, 28.1 mmol) was added K2CO3 (7.76 g, 56.2 mmol) and 4-chloro-2-iodo-thieno[3,2-c]pyridine-7-carbonitrile 26 (7.52 g, 23.4 mmol). The reaction was heated to 80° C. After 1.5 h, NMP was distilled away under reduced pressure. The resulting solids were suspended in H2O (500 mL) and filtered. The product was recrystallized from 350 mL of toluene to obtain 7.75 g of 27. 1H NMR (400 MHz, d6-DMSO) δ 8.58 (t, J=6 Hz, 1H), 8.35 (s, 1H), 8.17 (s, 1H), 7.28 (d, J=9 Hz, 2H), 6.89 (d, J=9 Hz, 2H), 4.68 (d, J=6 Hz, 2H), 3.37 (s, 3H).

Workup

  1. distillationNMP was distilled away under reduced pressure
  2. filtrationfiltered
  3. customThe product was recrystallized from 350 mL of toluene

Sources & evidence

ORD record
ord-ed55b1d240df441bb9def98b47dcab53
Source dataset
uspto-grants-2009_12
Patent number
US07635695B2

Reaction notes

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