Potassium Carbonate → HCID 18446520, compound

HRID 1868287Notes

Reaction equation

HRID 1868287 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+].[Br:17][C:18]1[S:26][C:25]2[C:24]([C:27]#[N:28])=[CH:23][N:22]=[C:21](Cl)[C:20]=2[CH:19]=1>CN1CCCC1=O>[Br:17][C:18]1[S:26][C:25]2[C:24]([C:27]#[N:28])=[CH:23][N:22]=[C:21]([NH:8][CH2:7][C:6]3[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C:20]=2[CH:19]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 754524-MethoxybenzylamineHCID 184465172-Bromo-4-chlorothieno[3,2-c]pyridine-7-carbonitrile

Product 1

HCID 18446520HCID 18446520, compoundYield 66.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

To a stirred solution of 4-methoxybenzylamine (1.2 equiv., 2.4 mmol) and K2CO3 (2.4 equiv., 4.8 mmol) in 5 mL anhydrous 1-methyl-2-pyrrolidinone was added 15 (1 equiv., 2 mmol). The mixture was heated at 130° C. under N2 for 1.5 h, allowed to cool, and the product precipitated by the addition of H2O (5 mL). The mixture was filtered, washed with water, and dried, yielding 16 (1.33 mmol) as a brown solid. 1H NMR (400 MHz, d6-DMSO) δ: 8.75 (1H, t, broad), 8.56 (1H, s), 8.21 (1H, s), 7.43 (2H, d, J=8.6 Hz), 7.04 (2H, d, J=8.6), 4.84 (2H, d, J=5.8), 3.88 (3H, s).

Workup

  1. temperatureto cool
  2. customthe product precipitated by the addition of H2O (5 mL)
  3. filtrationThe mixture was filtered
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-ed92b2d4f1f44faf9f9d2206b77c10c7
Source dataset
uspto-grants-2009_12
Patent number
US07635695B2

Reaction notes

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