1-Hydroxybenzotriazole → HCID 178509858, 화합물

HRID 1093816노트

반응식

HRID 1093816 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.[NH:51]1[CH2:56][CH2:55][CH:54]([O:57][C:58]2[CH:59]=[C:60]([CH:63]=[CH:64][CH:65]=2)[C:61]#[N:62])[CH2:53][CH2:52]1>CN(C=O)C.O>[C:61]([C:60]1[CH:59]=[C:58]([CH:65]=[CH:64][CH:63]=1)[O:57][CH:54]1[CH2:55][CH2:56][N:51]([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])[CH2:52][CH2:53]1)#[N:62]

참가 물질

8

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 534337453-(Piperidin-4-yloxy)benzonitrile hydrochlorideHCID 178525878HCID 178525878, 화합물

생성물 1

HCID 178509858HCID 178509858, 화합물수율 14.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

DIPEA (316 mg, 2.5 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (181 mg, 0.7 mmol) in DMF (3 mL) followed by HOBt (108 mg, 0.8 mmol) and EDCI.HCl (160 mg, 0.8 mmol). After 2 minutes of stirring, 3-(piperidin-4-yloxy)-benzonitrile hydrochloride (50 mg, 0.7 mmol) (prepared according to Step 1 and 5 of the General Scheme) was added and stirring was continued at ambient temperature overnight. The reaction mixture was diluted with water, extracted with ethyl acetate, washed with brine and concentrated The residue was purified by column chromatography (using neutral alumina and 5% MeOH in CHCl3) afford 44 mg (14.3% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-[4-(3-cyano-phenoxy)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 473.17, 99.16%, 1H NMR (300 MHz, DMSO-d6): δ 8.1 (m, 1H), 7.8 (m, 2H), 7.6 (m, 4H), 7.4 (m, 3H), 7.1 (b, 1H), 4.8 (m, 1H), 4.2 (m, 2H), 4.0 (m, 1H), 3.8 (m, 1H), 2.0 (m, 2H), 1.5 (m, 2H).

후처리

  1. additionwas added
  2. stirringstirring
  3. waitwas continued at ambient temperature overnight
  4. extractionextracted with ethyl acetate
  5. washwashed with brine
  6. concentrationconcentrated The residue
  7. customwas purified by column chromatography (using neutral alumina and 5% MeOH in CHCl3)

출처 및 근거

ORD 기록
ord-60f21ee701be492c8ff539a6b8b80404
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129376B2

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