Triethylamine → HCID 69480863, compound

HRID 2364309Notes

Reaction equation

HRID 2364309 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]1[C:6]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:7][CH:8]=[C:9]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[CH:10]=1.C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33]>ClCCl>[F:18][C:15]1[CH:16]=[CH:17][C:12]([CH2:11][C:9]2[CH:10]=[C:5]([NH:4][CH2:3][CH2:2][NH:1][S:32]([CH3:31])(=[O:34])=[O:33])[C:6]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:7][CH:8]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69480984HCID 69480984, compound

Product 1

HCID 69480863HCID 69480863, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cold (0° C.) solution of ethyl 3-[(2-aminoethyl)amino]-5-[(4-fluorophenyl)methyl]-2-pyridinecarboxylate (90 mg, 0.284 mmol) and triethylamine (59 μL, 0.426 mmol) in dichloromethane (1 mL) was added methanesulfonyl chloride (26 μL, 0.341 mmol) in dichloromethane (1 mL) dropwise. The reaction mixture was warmed to room temperature and stirred one hour. The reaction mixture was quenched with ice and diluted with dichloromethane. The organic layer was washed with water and brine, then dried over sodium sulfate. Filtration and concentration, followed by flash chromatography (0 to 5%, methanol in dichloromethane) provided ethyl 5-[(4-fluorophenyl)methyl]-3-({2-[(methylsulfonyl)amino]ethyl}amino)-2-pyridinecarboxylate as a clear oil. 1H NMR (400 MHz, CDCl3) δ 7.91 (s, 1 H), 7.87 (t, J=5.6 Hz, 1 H), 7.13 (dd, J=8.3, 5.5 Hz, 2 H), 6.97 (t, J=8.7 Hz, 2 H), 6.89 (s, 1 H), 4.93 (m, 1 H), 4.39 (q, J=7.1 Hz, 2 H), 3.91 (s, 2 H), 3.38 (m, 2 H), 3.33 (m, 2 H), 2.94 (s, 3 H), 1.41 (t, J=7.1 Hz, 3 H); MS m/z 396 (M+H)+.

Workup

  1. customThe reaction mixture was quenched with ice
  2. additiondiluted with dichloromethane
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-7b70e0409bc04acc998fa43b852d76b9
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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