Triethylamine → HCID 11260788, compound

HRID 916704Notes

Reaction equation

HRID 916704 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[C:14]([CH3:15])=[C:13]([C:16]3[CH:17]=[C:18]([C:22]([NH2:25])([CH3:24])[CH3:23])[CH:19]=[CH:20][CH:21]=3)[N:12]([CH3:26])[N:11]=2)=[CH:4][CH:3]=1.CCN(CC)CC.[F:34][C:35]([F:43])([F:42])[CH2:36][NH:37][S:38](Cl)(=[O:40])=[O:39]>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][C:10]2[C:14]([CH3:15])=[C:13]([C:16]3[CH:17]=[C:18]([C:22]([NH:25][S:38]([NH:37][CH2:36][C:35]([F:43])([F:42])[F:34])(=[O:40])=[O:39])([CH3:24])[CH3:23])[CH:19]=[CH:20][CH:21]=3)[N:12]([CH3:26])[N:11]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 13591655(2,2,2-Trifluoroethyl)sulfamyl chlorideHCID 58757348HCID 58757348, compound

Product 1

HCID 11260788HCID 11260788, compound

Procedure

Prepared by the procedure of Example 1 Step 3 using the amine from Step 3 (72 mg, 0.20 mmol), Et3N (114 μL, 0.82 mmol) and 2,2,2-trifluoroethylsulfamoyl chloride (121 mg, 0.61 mmol) to yield, after purification by column chromatography on silica using 80-100% Et2O/iso-hexanes the title sulfamide (23 mg, 22%). 1H NMR (CDCl3, 500 MHz) δ 7.54 (1H, d, J=7.8 Hz), 7.48 (1H, t, J=7.8 Hz), 7.42 (1H, s), 7.23 (1H, d, J=7.5 Hz), 7.19 (2H, dd, J=8.5, 5.6 Hz), 6.97 (2H, t, J=8.5 Hz), 4.71 (1H, s), 4.43 (1H, t, J=7.4 Hz), 3.74 (3H, s), 3.57 (2H, quintet, J=7.4 Hz), 2.98-2.92 (2H, m), 2.87-2.82 (2H, m), 1.87 (3H, s), 1.79 (6H, s). MS (ES+) C24H28F4N4O2S requires: 512, found: 513 (M+H+, 100%).

Workup

  1. customto yield
  2. customafter purification by column chromatography on silica using 80-100% Et2O/iso-hexanes the title sulfamide (23 mg, 22%)

Sources & evidence

ORD record
ord-8e1e1bf16c664593a14cfe53c28d03f5
Source dataset
uspto-grants-2007_09
Patent number
US07271191B2

Reaction notes

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