Triethylamine → HCID 58757362, compound

HRID 916691Notes

Reaction equation

HRID 916691 reaction equation
[F:1][C:2]([F:9])([F:8])[CH2:3][S:4](Cl)(=[O:6])=[O:5].[CH3:10][O:11][CH:12]([O:29][CH3:30])[C:13]1[CH:17]=[C:16]([C:18]2[CH:19]=[C:20]([C:24]([NH2:27])([CH3:26])[CH3:25])[CH:21]=[CH:22][CH:23]=2)[N:15]([CH3:28])[N:14]=1.CCN(CC)CC>C(Cl)Cl>[CH3:30][O:29][CH:12]([O:11][CH3:10])[C:13]1[CH:17]=[C:16]([C:18]2[CH:19]=[C:20]([C:24]([NH:27][S:4]([CH2:3][C:2]([F:9])([F:8])[F:1])(=[O:6])=[O:5])([CH3:26])[CH3:25])[CH:21]=[CH:22][CH:23]=2)[N:15]([CH3:28])[N:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 742422,2,2-Trifluoroethanesulfonyl chlorideHCID 58757354HCID 58757354, compound

Product 1

HCID 58757362HCID 58757362, compoundYield 53.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2,2,2-Trifluoroethylsulfonyl chloride (253 mg, 1.4 mmol) was added dropwise to a stirred solution of the amine from Step 2 (267 mg, 0.92 mmol) and Et3N (193 □L, 1.4 mmol) in CH2Cl2 (25 mL) at RT under N2. The mixture was stirred at RT for 30 min and then diluted with CH2Cl2 (25 mL), washed with NaHCO3 solution (20 mL) and concentrated under reduced pressure to yield the crude sulfonamide (213 mg, 53%). 1H NMR (CDCl3, 360 MHz) δ 7.60-7.53 (2H, m), 7.49 (1H, t, J=7.6 Hz), 7.37 (1H, d, J=7.6 Hz), 6.38 (1H, s), 5.50 (1H, s), 5.02 (1H, s), 3.88 (3H, s), 3.47 (2H, q, J=8.8 Hz), 3.44 (6H, s), 1.81 (6H, s). MS (ES+) C18H24F3N3O4S requires: 435, found: 404 (M-OCH3+, 100%).

Workup

  1. washwashed with NaHCO3 solution (20 mL)
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-3e52bea3c8ef488ea1141a54ff1db2d6
Source dataset
uspto-grants-2007_09
Patent number
US07271191B2

Reaction notes

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