Triethylamine → N-Cyclobutyl-N'-[1-(3-{1-ethyl-3-[(4-fluorophenoxy)methyl]-1H-pyrazol-5-yl}phenyl)-1-methylethyl]sulfamide
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][O: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.[CH:34]1([NH:38][S:39](Cl)(=[O:41])=[O:40])[CH2:37][CH2:36][CH2:35]1>>[CH:34]1([NH:38][S:39]([NH:17][C:14]([C:10]2[CH:11]=[CH:12][CH:13]=[C:8]([C:7]3[N:3]([CH2:1][CH3:2])[N:4]=[C:5]([CH2:18][O:19][C:20]4[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=4)[CH:6]=3)[CH:9]=2)([CH3:16])[CH3:15])(=[O:41])=[O:40])[CH2:37][CH2:36][CH2:35]1Participants
4
Reactant 3
Product 1
Procedure
Prepared by the procedure of Example 1 Step 3 using the amine from Step 5 (100 mg, 0.28 mmol), Et3N (114 mg, 1.1 mmol) and cyclobutylsulfamoyl chloride (192 mg, 1.1 mmol) to yield, after purification by column chromatography on silica using 70% Et2O/iso-hexanes and then by normal phase preparative HPLC, the sulfamide (17.5 mg, 12%). 1H NMR (CDCl3, 360 MHz) δ 7.60-7.52 (2H, m), 7.44 (1H, t, J=7.6 Hz), 7.30 (1H, d, J=7.6 Hz), 6.97 (4H, app. d, J=6.3 Hz), 6.37 (1H, s), 5.06 (2H, s), 4.55 (1H, s), 4.12 (2H, q, J=7.3 Hz), 3.78 (1H, app. sextet, J=8.3 Hz), 2.45-2.35 (2H, m), 1.93-1.82 (2H, m), 1.75 (6H, s), 1.72-1.60 (2H, m), 1.44 (3H, J=7.3 Hz). MS (ES+) C25H31FN4O3S requires: 486, found: 487 (M+H+, 100%).
Workup
- customto yield
- customafter purification by column chromatography on silica using 70% Et2O/iso-hexanes
Sources & evidence
- ORD record
- ord-bb3f88c72f584aa3a4e639d3791b6a41
- Source dataset
- uspto-grants-2007_09
- Patent number
- US07271191B2
Reaction notes
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