Triethylamine → HCID 11386158, compound

HRID 916706Notes

Reaction equation

HRID 916706 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[N:14]([CH3:15])[N:13]=[C:12]([C:16]3[CH:17]=[C:18]([CH:22]([NH2:24])[CH3:23])[CH:19]=[CH:20][CH:21]=3)[CH:11]=2)=[CH:4][CH:3]=1.[F:25][C:26]([F:34])([F:33])[CH2:27][NH:28][S:29](Cl)(=[O:31])=[O:30].CCN(CC)CC>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]2[N:14]([CH3:15])[N:13]=[C:12]([C:16]3[CH:17]=[C:18]([CH:22]([NH:24][S:29]([NH:28][CH2:27][C:26]([F:34])([F:33])[F:25])(=[O:31])=[O:30])[CH3:23])[CH:19]=[CH:20][CH:21]=3)[CH:11]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13591655(2,2,2-Trifluoroethyl)sulfamyl chlorideHCID 69426777HCID 69426777, compound

Product 1

HCID 11386158HCID 11386158, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

This amine was dissolved in CH2Cl2 (5 mL) and treated with 2,2,2-trifluoroethylsulfamoyl chloride (91 mg, 0.45 mmol) and Et3N (63 μL, 0.45 mmol) and stirred at RT for 30 min. The solvent was evaporated under reduced pressure and the residue purified by silica chromatography eluting with 2% MeOH/CH2Cl2 to yield the title sulfamide as a colourless gum (18 mg, 23% over 2 steps). 1H NMR (CDCl3, 500 MHz) δ 7.80-7.76 (1H, s), 7.65 (1H, d, J=7.8 Hz), 7.38 (1H, t, J=7.8 Hz), 7.23 (1H, d, J=7.8 Hz), 7.18-7.10 (2H, m), 6.98 (2H, t, J=8.7 Hz), 6.35 (1H, s), 4.66-4.56 (2H, m), 4.38-4.28 (1H, m), 3.69 (3H, s), 3.53-3.42 (1H, m), 3.42-3.30 (1H, m), 3.02-2.84 (4H, m), 1.62-1.52 (3H, m). MS (ES+) C22H24F4N4O2S requires: 484, found: 485 (M+H+).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue purified by silica chromatography
  3. washeluting with 2% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-46c1456ce87c452a83598842377094cc
Source dataset
uspto-grants-2007_09
Patent number
US07271191B2

Reaction notes

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