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

HRID 916708Notes

Reaction equation

HRID 916708 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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+).

Workup

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

Sources & evidence

ORD record
ord-760b7122962d4643b82aedec980d1b11
Source dataset
uspto-grants-2007_09
Patent number
US07271191B2

Reaction notes

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