(4S)-(4-methyl-2,5-dioxoimidazolidin-4-yl)methanesulphonyl chloride → (5S)-5-Methyl-5-[({4-[4-(2,2,3,3,3-pentafluoropropoxy)phenoxy]-piperidin-1-yl}sulphonyl)methyl]imidazolidine-2,4-dione

HRID 1091990노트

반응식

HRID 1091990 반응식
[CH3:1][C@@:2]1([CH2:9][S:10](Cl)(=[O:12])=[O:11])[C:6](=[O:7])[NH:5][C:4](=[O:8])[NH:3]1.Cl.[F:15][C:16]([F:36])([C:32]([F:35])([F:34])[F:33])[CH2:17][O:18][C:19]1[CH:31]=[CH:30][C:22]([O:23][CH:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)=[CH:21][CH:20]=1>ClCCl.C(N(CC)CC)C>[CH3:1][C@:2]1([CH2:9][S:10]([N:27]2[CH2:28][CH2:29][CH:24]([O:23][C:22]3[CH:21]=[CH:20][C:19]([O:18][CH2:17][C:16]([F:15])([F:36])[C:32]([F:34])([F:35])[F:33])=[CH:31][CH:30]=3)[CH2:25][CH2:26]2)(=[O:12])=[O:11])[NH:3][C:4](=[O:8])[NH:5][C:6]1=[O:7]

참가 물질

5

반응물 2

HCID 16738713(4S)-(4-methyl-2,5-dioxoimidazolidin-4-yl)methanesulphonyl chlorideHCID 866246564-{4-(2,2,3,3,3-Pentafluoropropoxy)phenoxy]-piperidine hydrochloride

생성물 1

HCID 11519157(5S)-5-Methyl-5-[({4-[4-(2,2,3,3,3-pentafluoropropoxy)phenoxy]-piperidin-1-yl}sulphonyl)methyl]imidazolidine-2,4-dione수율 17.8%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

실험 절차

[(4S)-4-methyl-2,5-dioxoimidazolidin-4-yl]methanesulphonyl chloride (0.188 g) was added to a solution of 4-{4-(2,2,3,3,3-pentafluoropropoxy)phenoxy]-piperidine hydrochloride (0.30 g) in dichloromethane (10 ml) and triethylamine (0.70 ml) at ambient temperature. Stirred for 16 hours and evaporated to dryness. The residue was purified by prep HPLC (using λ230 nm as the detecting wavelength) eluting with 0-95% acetonitrile, H2O, +0.2% trifluoroacetic acid. Yielded a solid product, which was dried under vacuum at 50° C. to give the title compound (0.076 g). NMR: (DMSOd6) δ 10.7 (s, 1H), 8.0 (s, 1H), 7.0 (m, 4H), 4.75 (t, 2H), 4.45 (m, 1H), 3.5 (d, 1H), 3.3 (m, 3H), 3.1 (m, 2H), 1.95 (m, 2H), 1.7 (m, 2H), 1.35 (s, 3H). Mass Spectrum: M−H− 513.

후처리

  1. customevaporated to dryness
  2. customThe residue was purified by prep HPLC (
  3. washeluting with 0-95% acetonitrile, H2O, +0.2% trifluoroacetic acid
  4. customYielded a solid product, which
  5. customwas dried under vacuum at 50° C.

출처 및 근거

ORD 기록
ord-b2f94d880dfc474a949b7e1821789139
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129412B2

반응 노트

불러오는 중…