Potassium Carbonate → HCID 69219351, compound

HRID 272729Notes

Reaction equation

HRID 272729 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[C:17](=[O:18])[NH:16][C:15]4[CH:19]=[C:20]([CH2:23][CH2:24][O:25][C:26]5[CH:31]=[CH:30][C:29]([N:32]6[CH2:37][CH2:36][O:35][CH2:34][CH2:33]6)=[CH:28][CH:27]=5)[CH:21]=[CH:22][C:14]=4[NH:13][C:12]=3[CH:38]=2)=[CH:4][C:3]=1[O:39][CH3:40].Cl.Cl[CH2:43][C:44]1[CH:49]=[CH:48][N:47]=[CH:46][CH:45]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH3:40][O:39][C:3]1[CH:4]=[C:5]([C:8]2[CH:9]=[CH:10][C:11]3[C:17](=[O:18])[NH:16][C:15]4[CH:19]=[C:20]([CH2:23][CH2:24][O:25][C:26]5[CH:31]=[CH:30][C:29]([N:32]6[CH2:33][CH2:34][O:35][CH2:36][CH2:37]6)=[CH:28][CH:27]=5)[CH:21]=[CH:22][C:14]=4[NH:13][C:12]=3[CH:38]=2)[CH:6]=[CH:7][C:2]=1[O:1][CH2:43][C:44]1[CH:49]=[CH:48][N:47]=[CH:46][CH:45]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 745704-(Chloromethyl)pyridinium chlorideHCID 69218777HCID 69218777, compound

Product 1

HCID 69219351HCID 69219351, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of Example 474 (26.9 mg, 0.05 mmol) and 4-chloromethylpyridine hydrochloride (24.6 mg, 0.15 mmol) in DMF (1 mL) was treated with K2CO3 (34.6 mg, 0.25 mmol) and heated at 80° C. for 7 hours. The reaction mixture was then cooled to room temperature, diluted with ethyl acetate, washed with water and brine, dried (MgSO4), filtered, and concentrated under vacuum. The residue was purified by preparative HPLC to provide the title compound as the di-TFA salt. MS (ESI) m/e 629 (M+H)+; 1H NMR (300 MHz, DMSO-d6) 9.77 (s, 1H), 8.79 (br s, 2H), 7.85 (s, 1H), 7.8 (d, J=4.1 Hz, 2H), 7.73 (d, J=8.5 Hz, 1H), 7.26 (dd, J=3.6, 1.9 Hz, 2H), 7.08-7.20 (m, 3H), 6.82-6.95 (m, 7H), 5.38 (s, 2H), 4.04 (t, J=6.8 Hz, 2H), 3.91 (s, 3H), 3.71-3.74 (m, 4H), 2.99-3.02 (m, 4H), 2.86 (t, J=6.8 Hz, 2H).

Workup

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. washwashed with water and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-51e921a3b38440b9b2a85df84f19aa13
Source dataset
uspto-grants-2008_11
Patent number
US07456169B2

Reaction notes

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