2-Pyridinemethanamine → HCID 57541262, compound

HRID 1514631Notes

Reaction equation

HRID 1514631 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1.[Cl:9][C:10]1[CH:11]=[C:12]2[C:20](=[O:21])[C:19]3[CH:22]=[C:23]([CH2:26][S:27](N(C)C4C=CC=CC=4)(=[O:29])=[O:28])[CH:24]=[CH:25][C:18]=3[CH:17]=[CH:16][C:13]2=[N:14][CH:15]=1.C(=O)([O-])O.[Na+]>CN1CCCC1=O>[Cl:9][C:10]1[CH:11]=[C:12]2[C:20](=[O:21])[C:19]3[CH:22]=[C:23]([CH2:26][S:27]([NH:1][CH2:2][C:3]4[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=4)(=[O:29])=[O:28])[CH:24]=[CH:25][C:18]=3[CH:17]=[CH:16][C:13]2=[N:14][CH:15]=1

Participants

5

Reactant 3

HCID 195092-PyridinemethanamineHCID 516892Sodium BicarbonateHCID 57541245HCID 57541245, compound

Product 1

HCID 57541262HCID 57541262, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
132.5 °C

Procedure

2-Aminomethylpyridine (55.9 ml, 546 mmol) was added to a solution of 1-(3-chloro-5-oxo-5H-benzo[4,5]cyclohepta[1,2-b]pyridin-7-yl)-N-methyl-N-phenylmethanesulfonamide (51.6 g, 121 mmol) in N-methyl-2-pyrrolidinone (1214 ml) at room temperature. The solution was then heated to 130-135° C. for 2 h in a pre-warmed oil bath. The solution was then cooled to room temperature and poured into aqueous sodium hydrogen carbonate (saturated, 3.0 L) and 500 mL ice-water and extracted with ethyl acetate (3×500 mL). The combined organics were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (EtOAc/Hexanes gradient) to afford the title compound as a yellow solid. 1H NMR (600 MHz, DMSO-D6) δ 8.99 (d, 1H); 8.47 (d, 1H); 8.46 (m, 1H); 8.16 (d, 1H); 7.81 (m, 3H); 7.76 (m, 1H); 7.49 (d, 1H); 7.38 (d, 1H); 7.32 (d, 1H); 7.25 (m, 1H); 4.63 (s, 2H); 4.22 (d, 2H). LRMS (APCI) calculated for C21H17ClN3O3S [M+H]+, 426.1. found 426.0.

Workup

  1. temperatureThe solution was then cooled to room temperature
  2. extractionextracted with ethyl acetate (3×500 mL)
  3. dry with materialThe combined organics were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (EtOAc/Hexanes gradient)

Sources & evidence

ORD record
ord-732fe328b5404d8386edeeb2f0724471
Source dataset
uspto-grants-2012_07
Patent number
US08222269B2

Reaction notes

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