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1-Hydroxybenzotriazole → HCID 178504712、化合物

HRID 1093754
ノート
印刷プレビュー

反応式

HRID 1093754 の反応式
CCN(C(C)C)C(C)C.[C:10]1([C:16]2[NH:20][N:19]=[C:18]([C:21]([NH:23][CH2:24][C:25]([OH:27])=O)=[O:22])[CH:17]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.[CH3:51][S:52]([C:55]1[CH:67]=[CH:66][CH:65]=[CH:64][C:56]=1[O:57][CH:58]1[CH2:63][CH2:62][NH:61][CH2:60][CH2:59]1)(=[O:54])=[O:53]>CN(C=O)C.O>[CH3:51][S:52]([C:55]1[CH:67]=[CH:66][CH:65]=[CH:64][C:56]=1[O:57][CH:58]1[CH2:59][CH2:60][N:61]([C:25](=[O:27])[CH2:24][NH:23][C:21]([C:18]2[CH:17]=[C:16]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:20][N:19]=2)=[O:22])[CH2:62][CH2:63]1)(=[O:54])=[O:53]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 665924674-(2-(Methylsulfonyl)phenoxy)piperidine hydrochlorideHCID 178525878HCID 178525878、化合物

生成物 1

HCID 178504712HCID 178504712、化合物
収率 35.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

DIPEA (63 mg, 0.48 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (40 mg, 0.163 mmol) in DMF (1 mL) followed by HOBt (26 mg, 0.195 mmol) and EDCI.HCl (37 mg, 0.195 mmol). After 2 minutes 4-(2-methanesulfonyl-phenoxy)-piperidine hydrochloride (57 mg, 0.195 mmol) was added to the reaction mixture and stirring was continued at ambient temperature overnight. The reaction mixture was diluted with cold water and extracted with ethyl acetate. The ethyl acetate was washed with brine solution, dried over sodium sulfate and concentrated under reduced pressure The residue was purified by preparative HPLC to afford 28 mg (26.66% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(2-methanesulfonyl-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 483, 98.59%. 1H NMR (300 MHz, CDCl3): δ 8.8 (bs, 1H), 8.0 (m, 1H), 7.7-7.6 (d, 2H), 7.6-7.5 (m, 1H), 7.5-7.3 (m, 3H), 7.2-7.0 (m, 3H), 5.1-4.9 (m, 3H), 4.6-4.5 (dd, 1H), 4.2-4.1 (m, 2H), 3.9-3.4 (m, 3H), 3.2 (s, 3H), 2.1-1.9 (m, 4H).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate was washed with brine solution
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure The residue
  5. customwas purified by preparative HPLC

出典と根拠

ORDレコード
ord-dcf236c2380144ad98c040d74e76ee4c
出典データセット
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08129376B2

反応ノート

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