Pyridine → HCID 19788721, compound

HRID 1656591Notes

Reaction equation

HRID 1656591 reaction equation
[NH2:1][C:2]1[CH:29]=[CH:28][C:5]([O:6][CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:19][CH:18]=3)=[O:16])[CH2:11][CH2:10]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>ClCCl>[CH3:27][S:24]([NH:23][C:20]1[CH:21]=[CH:22][C:17]([C:15]([CH:12]2[CH2:11][CH2:10][N:9]([CH2:8][CH2:7][O:6][C:5]3[CH:4]=[CH:3][C:2]([NH:1][S:37]([CH3:36])(=[O:39])=[O:38])=[CH:29][CH:28]=3)[CH2:14][CH2:13]2)=[O:16])=[CH:18][CH:19]=1)(=[O:26])=[O:25]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 19769862HCID 19769862, compound

Product 1

HCID 19788721HCID 19788721, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a stirring solution of the amine (1.20 g, 2.88 mmol) prepared in the preceding paragraph in dichloromethane (20 mL) at 0° C. under nitrogen was added pyridine (0.47 mL, 5.76 mmol) and methanesulfonyl chloride (0.33 mL, 4.32 mmol). The mixture was stirred at 25° C. for 2 hours and was then partitioned between 5% aqueous sodium bicarbonate and 4:1 dichloromethane/isopropanol. The organic phase was dried (MgSO4), decolorized (charcoal) and concentrated to afford a residue which was triturated with ethyl acetate/diethyl ether/hexane to give the title compound as a white solid: 0.92 g (65%). mp 168°-172° C.; 1H NMR (DMSO-d6): δ 10.28 & 9.35 (2s, 2H), 7.94 (d, J=8.87 Hz, 2H), 7.27 (d, J=8.85 Hz, 2H), 7.13 (d, J=9.00 Hz, 2H), 6.92 (d, J=9.01 Hz, 2H), 4.05 (t, J=5.61 Hz, 2H), 3.32 (m, 1H), 3.09 (s, 3H), 3.00 (m, 2H), 2.86 (s, 3H), 2.75 (m, 2H), 2.30 (m, 2H), 1.75-1.50 (m, 4H). IR (KBr): 3220, 1660 cm-1 ; MS (m/z) 496 (MH+), 217,91.

Workup

  1. customwas then partitioned between 5% aqueous sodium bicarbonate and 4:1 dichloromethane/isopropanol
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated
  4. customto afford a residue which
  5. customwas triturated with ethyl acetate/diethyl ether/hexane

Sources & evidence

ORD record
ord-7ee4367a422e491e90ea53e216ea4723
Source dataset
uspto-grants-1993_10
Patent number
US05254689

Reaction notes

Loading…