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1-Hydroxybenzotriazole → HCID 178523479, 화합물

HRID 1093820
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HRID 1093820 반응식
CCN(C(C)C)C(C)C.[F:10][C:11]([F:31])([F:30])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[NH:22][N:21]=[C:20]([C:23]([NH:25][CH2:26][C:27]([OH:29])=O)=[O:24])[CH:19]=1.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.Cl.Cl.Cl.[Cl:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=1[NH:63][CH:64]1[CH2:69][CH2:68][NH:67][CH2:66][CH2:65]1>CN(C=O)C.O>[Cl:56][C:57]1[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=1[NH:63][CH:64]1[CH2:69][CH2:68][N:67]([C:27](=[O:29])[CH2:26][NH:25][C:23]([C:20]2[CH:19]=[C:18]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=3[C:11]([F:10])([F:31])[F:30])[NH:22][N:21]=2)=[O:24])[CH2:66][CH2:65]1
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참가 물질

8

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66591362HCID 66591362, 화합물HCID 178525877HCID 178525877, 화합물

생성물 1

HCID 178523479HCID 178523479, 화합물
수율 44.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

DIPEA (137 mg, 1.06 mmol) was added to a stirred solution {[5-(2-trifluoromethyl-phenyl)-1H-pyrazole-3-carbonyl]-amino}-acetic acid (95 mg, 0.3 mmol) (prepared by the method used for the synthesis of Intermediate 30, starting from (2′-trifluoromethyl)acetophenone) in DMF (2.0 mL) followed by HOBt (47 mg, 0.35 mmol) and EDCI.HCl (67 mg, 0.35 mmol). After 2 minutes of stirring, (2-chloro-phenyl)-piperidin-4-yl-amine dihydrochloride (75 mg, 0.3 mmol) 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 under reduced pressure. The residue was purified washing with diethyl ether to afford 67 mg (43.5% Yield) of 5-(2-trifluoromethyl-phenyl)-1H-pyrazole-3-carboxylic acid {2-[4-(2-chloro-phenylamino)-piperidin-1-yl]-2-oxo-ethyl}-amide. LC/MS [M+H]+: 506.12, 97.9%, 1H NMR (300 MHz, DMSO-d6): δ13.2 (d, 1H), 8.2 (m, 1H), 7.5 (m, 5H), 7.2 (m, 2H), 6.85 (m, 1H), 6.5 (m, 2H), 4.8 (m, 1H), 4.3 (m, 1H), 4.1 (d, 2H), 4.0 (m, 1H), 3.6 (m, 1H), 3.2 (m, 1H), 2.7 (m, 1H), 1.9 (m, 2H), 1.3 (m, 2H).

후처리

  1. customprepared by the method
  2. stirringstirring
  3. waitwas continued at ambient temperature overnight
  4. extractionextracted with ethyl acetate
  5. washwashed with brine
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified
  8. washwashing with diethyl ether

출처 및 근거

ORD 기록
ord-c242a05837114e88a5f965d8b93b049f
출처 데이터셋
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08129376B2

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