(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 1091990ノート

反応式

HRID 1091990 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

[(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.

後処理

  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.

出典と根拠

ORDレコード
ord-b2f94d880dfc474a949b7e1821789139
出典データセット
uspto-grants-2012_03
特許番号
US08129412B2

反応ノート

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