Methanesulfonic Acid → HCID 12082302, compound

HRID 1358694Notes

Reaction equation

HRID 1358694 reaction equation
CS(O)(=O)=O.C(OC([N:13]1[CH2:18][CH2:17][C:16]2=[N:19][N:20]([CH2:23][C:24]([F:27])([F:26])[F:25])[C:21](=[O:22])[C:15]2([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)[CH2:14]1)=O)(C)(C)C.C(N(CC)CC)C>C(Cl)Cl>[N:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[CH2:28][C:15]12[C:21](=[O:22])[N:20]([CH2:23][C:24]([F:26])([F:27])[F:25])[N:19]=[C:16]1[CH2:17][CH2:18][NH:13][CH2:14]2

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 8471TriethylamineHCID 12082301HCID 12082301, compound

Product 1

HCID 12082302HCID 12082302, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Methanesulfonic acid (11.6 g, 121 mmol) was added dropwise to a solution of the product from step B (10 g, 24.2 mmol) in CH2Cl2 (100 mL) over about 30 minutes. The reaction mixture was stirred for about 1 hour, then cooled to about 0° C., and then triethylamine (18.6 mL, 133.1 mmol) was added through an addition funnel. The mixture was allowed to warm to room temperature over about 1 hour, diluted with additional CH2Cl2 and washed with saturated aqueous NaCl, dried over Na2SO4, filtered and concentrated in vacuo to afford the product as a white solid (7.2 g). 1H-NMR (CDCl3) δ: 2.51-2.72 (m, 4H), 3.35 (m, 2H), 3.49 (m, 2H), 4.03 (m, 1H), 4.25 (m, 1H), 7.08 (d, 2H), 7.51 (t, 1H), 8.37 (d, 1H).

Workup

  1. temperatureto warm to room temperature over about 1 hour
  2. washwashed with saturated aqueous NaCl
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1cb7be996270428089e0bac3922af320
Source dataset
uspto-grants-2003_07
Patent number
US06596867B2

Reaction notes

Loading…