1-Hydroxybenzotriazole → HCID 178523491, 화합물

HRID 1093815

반응식

HRID 1093815 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.FC(F)(F)C(O)=O.[F:57][C:58]([F:73])([F:72])[C:59]1[CH:71]=[CH:70][CH:69]=[CH:68][C:60]=1[O:61][CH:62]1[CH2:67][CH2:66][NH:65][CH2:64][CH2:63]1>CN(C=O)C.O>[O:27]=[C:25]([N:65]1[CH2:64][CH2:63][CH:62]([O:61][C:60]2[CH:68]=[CH:69][CH:70]=[CH:71][C:59]=2[C:58]([F:57])([F:72])[F:73])[CH2:67][CH2:66]1)[CH2:24][NH:23][C:21]([C:18]1[CH:17]=[C:16]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:20][N:19]=1)=[O:22]

참가 물질

8

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 866346354-(2-Trifluoromethyl-phenoxy)-piperidine trifluoracetateHCID 178525878HCID 178525878, 화합물

생성물 1

HCID 178523491HCID 178523491, 화합물수율 58.7%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

DIPEA (154 mg, 1.2 mmol) was added to a stirred solution of [(5-phenyl-1H-pyrazole-3-carbonyl)-amino]-acetic acid (100 mg, 0.4 mmol) in DMF (2.0 mL) followed by HOBt (60 mg, 0.49 mmol) and EDCI.HCl (93 mg, 0.49 mmol). After 2 minutes of stirring, 4-(2-trifluoromethyl-phenoxy)-piperidine trifluoroacetate (167 mg, 0.49 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 ethylacetate, washed with brine and concentrated to afford 111 mg (57.81% Yield) of 5-phenyl-1H-pyrazole-3-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-phenoxy)-piperidin-1-yl]-ethyl}-amide. LC/MS [M+H]+: 473.17, 97.38%, 1H NMR (300 MHz, DMSO-d6): δ13.8 (m, 1H), 8.1 (bs, 1H), 7.9-7.3 (m, 8H), 7.2-7.0 (m, 2H), 4.9 (bs, 1H), 4.2 (m, 2H), 3.8-2.9 (m, 4H), 2.0-1.7 (m, 3H).

후처리

  1. additionwas added
  2. stirringstirring
  3. waitwas continued at ambient temperature overnight
  4. extractionextracted with ethylacetate
  5. washwashed with brine
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-2f425a5334334c5aa616200f2d8d7dff
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129376B2

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