Sodium Carbonate → HCID 56597329, compound

HRID 2174955Notes

Reaction equation

HRID 2174955 reaction equation
[C:1]([N:3]=[C:4]1[N:19]([CH3:20])[C:7]2[CH:8]=[N:9][C:10]3[CH:11]=[CH:12][C:13](B(O)O)=[CH:14][C:15]=3[C:6]=2[N:5]1[C:21]1[CH:22]=[N:23][C:24]([C:27]([C:30]#[N:31])([CH3:29])[CH3:28])=[CH:25][CH:26]=1)#[N:2].Br[C:33]1[C:34]([CH3:43])=[CH:35][C:36]([NH:39][C:40](=[O:42])[CH3:41])=[N:37][CH:38]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[C:1]([N:3]=[C:4]1[N:19]([CH3:20])[C:7]2[CH:8]=[N:9][C:10]3[CH:11]=[CH:12][C:13]([C:33]4[C:34]([CH3:43])=[CH:35][C:36]([NH:39][C:40](=[O:42])[CH3:41])=[N:37][CH:38]=4)=[CH:14][C:15]=3[C:6]=2[N:5]1[C:21]1[CH:22]=[N:23][C:24]([C:27]([C:30]#[N:31])([CH3:29])[CH3:28])=[CH:25][CH:26]=1)#[N:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 15179563N-(5-Bromo-4-methylpyridin-2-yl)acetamideHCID 86683445HCID 86683445, compound

Product 1

HCID 56597329HCID 56597329, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
111 °C

Procedure

To the stirred solution 2-(cyanoimino)-1-(6-(2-cyanopropan-2-yl)pyridin-3-yl)-3-methyl-2,3-dihydro-1H-imidazo[4,5-c]quinolin-8-ylboronic acid (0.390 mmol) in dry DMF (5 mL) was added N-(5-bromo-4-methylpyridin-2-yl)acetamide (0.390 mmol) followed by catalyst palladium dichlorobis triphenylphosphine (0.039 mmol). Saturated solution of sodium carbonate (0.780 mmol) was added to it and the resulting solution was heated to 111° C. for 8 minutes in microwave. Solvent was evaporated and the crude material was extracted in EtOAc, washed with brine several times and dried over anhydrous Na2SO4. The solvent was evaporated and the crude solid was purified (silica gel column, CHCl3/MeOH as eluent) to obtain the title compound. 1H NMR (300 MHz, DMSO-d6): δ 10.46 (s, 1H), 9.26 (s, 1H), 9.02 (d, J=2.4 Hz, 1H), 8.35 (dd, J=2.4, 8.4 Hz, 1H), 8.17 (d, J=8.7 Hz, 1H), 7.91 (m, 3H), 7.70 (dd, J=1.8, 8.7 Hz, 1H), 6.60 (s, 1H), 3.90 (s, 3H), 2.08 (s, 3H), 2.00 (s, 3H), 1.70 (s, 6H); MS (m/z): 516 (M+1)+.

Workup

  1. customSolvent was evaporated
  2. extractionthe crude material was extracted in EtOAc
  3. washwashed with brine several times
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe solvent was evaporated
  6. customthe crude solid was purified (silica gel column, CHCl3/MeOH as eluent)

Sources & evidence

ORD record
ord-f112e20dbfff44618c1d7303e94be031
Source dataset
uspto-grants-2015_06
Patent number
US09062046B2

Reaction notes

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