Triethylamine → n-Cyclobutyl-n'-(1-{3-[3-(4-fluorobenzyl)-1-methyl-1h-pyrazol-5-yl]phenyl}-1-methylethyl)sulfamide

HRID 916708ノート

反応式

HRID 916708 の反応式
[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH2:6][C:7]2[CH:11]=[C:10]([C:12]3[CH:13]=[C:14]([C:18]([NH2:21])([CH3:20])[CH3:19])[CH:15]=[CH:16][CH:17]=3)[N:9]([CH3:22])[N:8]=2)=[CH:4][CH:3]=1.CCN(CC)CC.[CH:32]1([NH:36][S:37](Cl)(=[O:39])=[O:38])[CH2:35][CH2:34][CH2:33]1>C(Cl)Cl>[CH:32]1([NH:36][S:37]([NH:21][C:18]([C:14]2[CH:15]=[CH:16][CH:17]=[C:12]([C:10]3[N:9]([CH3:22])[N:8]=[C:7]([CH2:6][C:5]4[CH:23]=[CH:24][C:2]([F:1])=[CH:3][CH:4]=4)[CH:11]=3)[CH:13]=2)([CH3:20])[CH3:19])(=[O:39])=[O:38])[CH2:35][CH2:34][CH2:33]1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 22326606N-cyclobutylsulfamoyl chlorideHCID 694304121-{3-[3-(4-Fluorobenzyl)-1-methyl-1h-pyrazol-5-yl]-phenyl}-1-methylethylamine

生成物 1

HCID 11751461n-Cyclobutyl-n'-(1-{3-[3-(4-fluorobenzyl)-1-methyl-1h-pyrazol-5-yl]phenyl}-1-methylethyl)sulfamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

The crude amine was dissolved in CH2Cl2 (5 mL) and Et3N (222 μL, 1.6 mmol) and crude cyclobutylsulfamoyl chloride (136 mg, ca. 0.8 mmol) were added and the reaction was stirred at RT for 30 min. The reaction was evaporated under reduced pressure and diluted with MeCN:DMSO (1:1, 2 mL) and filtered. The filtrate was injected on to a reverse phase HPLC system and the title compound was isolated, after basic workup, as a yellow gum (4 mg, 1% over 2 steps). 1H NMR (CDCl3, 500 MHz) δ 7.52-7.48 (2H, m), 7.41 (1H, t, J=8.6 Hz), 7.31-7.23 (3H, m), 6.98 (2H, t, J=8.8 Hz), 6.02 (1H, s), 4.49 (1H, s), 4.10 (1H, d, J=8.4 Hz), 3.96 (2H, s), 3.85 (3H, s), 3.82-3.73 (1H, m), 2.30-2.21 (2H, m), 1.90-1.79 (2H, m), 1.73 (6H, s), 1.72-1.63 (2H, m). MS (ES+) C24H29FN4O2S requires 456: found: 457 (M+H+).

後処理

  1. customThe reaction was evaporated under reduced pressure
  2. additiondiluted with MeCN:DMSO (1:1, 2 mL)
  3. filtrationfiltered

出典と根拠

ORDレコード
ord-760b7122962d4643b82aedec980d1b11
出典データセット
uspto-grants-2007_09
特許番号
US07271191B2

反応ノート

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