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1-Hydroxybenzotriazole → HCID 178504712, 화합물

HRID 1093754
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HRID 1093754 반응식
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]
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참가 물질

8

반응물 5

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

생성물 1

HCID 178504712HCID 178504712, 화합물
수율 35.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-dcf236c2380144ad98c040d74e76ee4c
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08129376B2

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