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

HRID 916708노트

반응식

HRID 916708 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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+).

후처리

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

출처 및 근거

ORD 기록
ord-760b7122962d4643b82aedec980d1b11
출처 데이터셋
uspto-grants-2007_09
특허 번호
US07271191B2

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