Triethylamine → HCID 11328887, compound

HRID 916710Notes

Reaction equation

HRID 916710 reaction equation
[F:1][C:2]([F:10])([F:9])[CH2:3][NH:4][S:5](Cl)(=[O:7])=[O:6].[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:22]([CH3:23])[N:21]=[C:20]([C:24]3[CH:25]=[C:26]([C:30]([NH2:33])([CH3:32])[CH3:31])[CH:27]=[CH:28][CH:29]=3)[CH:19]=2)=[CH:14][CH:13]=1.CCN(CC)CC>C(Cl)Cl>[F:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[N:22]([CH3:23])[N:21]=[C:20]([C:24]3[CH:25]=[C:26]([C:30]([NH:33][S:5]([NH:4][CH2:3][C:2]([F:10])([F:9])[F:1])(=[O:7])=[O:6])([CH3:31])[CH3:32])[CH:27]=[CH:28][CH:29]=3)[CH:19]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13591655(2,2,2-Trifluoroethyl)sulfamyl chlorideHCID 58757353HCID 58757353, compound

Product 1

HCID 11328887HCID 11328887, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2,2,2-Trifluoroethylsulfamoyl chloride (53 mg, 0.3 mmol) was added dropwise to a stirred solution of the amine from Step 4 (50 mg, 0.2 mmol) and Et3N (37 μL, 0.3 mmol) in CH2Cl2 (2 m]L) at RT under N2. The mixture was stirred at RT overnight and then diluted with CH2Cl2 (25 mL), washed with NaHCO3 solution (20 m L), dried (MgSO4) and concentrated under reduced pressure. The crude product was purified by column chromatography on silica eluting with 20% EtOAc/iso-hexane to yield the title sulfamide (5 mg, 6%). 1H NMR (CDCl3, 500 MHz) δ 8.02 (1H, s), 7.69 (1H, d, J=6.6 Hz), 7.45-7.42 (4H, m), 7.18 (2H, t, J=8.6 Hz), 6.58 (1H, s), 4.70 (1H, s), 4.30-4.27 (1H, m), 3.90 (3H, s), 3.57-3.53 (2H, m), 1.80 (6H, s). MS (ES+) C21H22F4N4O2S requires: 470, found: 471 (M+H+, 100%).

Workup

  1. washwashed with NaHCO3 solution (20 m L)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by column chromatography on silica eluting with 20% EtOAc/iso-hexane

Sources & evidence

ORD record
ord-202c38a372854b41b42828b39bf20085
Source dataset
uspto-grants-2007_09
Patent number
US07271191B2

Reaction notes

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