Triethylamine → HCID 11752617, compound

HRID 916701Notes

Reaction equation

HRID 916701 reaction equation
[CH2:1]([N:3]1[C:7]([C:8]2[CH:9]=[C:10]([C:14]([NH2:17])([CH3:16])[CH3:15])[CH:11]=[CH:12][CH:13]=2)=[CH:6][C:5]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[N:4]1)[CH3:2].CCN(CC)CC.[F:34][C:35]([F:43])([F:42])[CH2:36][NH:37][S:38](Cl)(=[O:40])=[O:39]>>[CH2:1]([N:3]1[C:7]([C:8]2[CH:9]=[C:10]([C:14]([NH:17][S:38]([NH:37][CH2:36][C:35]([F:43])([F:42])[F:34])(=[O:40])=[O:39])([CH3:16])[CH3:15])[CH:11]=[CH:12][CH:13]=2)=[CH:6][C:5]([CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)=[N:4]1)[CH3:2]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 13591655(2,2,2-Trifluoroethyl)sulfamyl chlorideHCID 58757366HCID 58757366, compound

Product 1

HCID 11752617HCID 11752617, compound

Procedure

Prepared by the procedure of Example 1 Step 3. The amine from Step 3 (67 mg, 0.19 mmol), Et3N (80 □L, 0.57 mmol) and 2,2,2-trifluoroethylsulfamoyl chloride (75 mg, 0.38 mmol) were reacted to yield after purification by column chromatography on silica using 80% Et2O/iso-hexanes the title sulfamide (25 mg, 26%). 1H NMR (CDCl3, 500 MHz) δ 7.57-7.49 (2H, m), 7.45 (1H, t, J=7.8 Hz), 7.30 (1H, d, J=7.8 Hz), 7.19 (2H, dd, J=8.7, 5.6 Hz), 6.97 (2H, t J=8.7 Hz), 6.03 (1H, s), 4.69 (1H, s), 4.39 (1H, t, J=5.4 Hz), 4.10 (2H, q, J=7.2 Hz), 3.57 (2H, quintet, J=5.4 Hz), 3.03-2.90 (4H, m), 1.78 (6H, s), 1.39 (3H, t, J=7.2 Hz). MS (ES+) C24H28F4N4O2S requires: 512, found: 513 (M+H+, 100%).

Workup

  1. customPrepared by the procedure of Example 1 Step 3
  2. customto yield
  3. customafter purification by column chromatography on silica using 80% Et2O/iso-hexanes the title sulfamide (25 mg, 26%)

Sources & evidence

ORD record
ord-51fab35615f64d2eba91966a6239a7be
Source dataset
uspto-grants-2007_09
Patent number
US07271191B2

Reaction notes

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