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Trifluoroacetic acid → HCID 59559584, 화합물

HRID 1177851
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HRID 1177851 반응식
CCN(C(C)C)C(C)C.[C:10]1([NH:16][C:17]2[CH:25]=[CH:24][C:20]([C:21]([OH:23])=O)=[CH:19][CH:18]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH2:47][CH2:48][C:49]([N:51]1[CH2:56][CH2:55][N:54]([C:57](=[O:66])[C:58]2[CH:63]=[CH:62][C:61]([Cl:64])=[CH:60][C:59]=2[Cl:65])[CH2:53][CH2:52]1)=[O:50].C(O)(C(F)(F)F)=O>CN(C=O)C.O>[Cl:65][C:59]1[CH:60]=[C:61]([Cl:64])[CH:62]=[CH:63][C:58]=1[C:57]([N:54]1[CH2:53][CH2:52][N:51]([C:49](=[O:50])[CH2:48][NH:47][C:21](=[O:23])[C:20]2[CH:19]=[CH:18][C:17]([NH:16][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[CH:25][CH:24]=2)[CH2:56][CH2:55]1)=[O:66]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 6

HCID 6422Trifluoroacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2923314-(Phenylamino)benzoic acidHCID 2756402HCID 2756402, 화합물

생성물 1

HCID 59559584
HCID 59559584, 화합물
수율 53%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

DIPEA (133 mg, 0.18 mL, 0.56 mmol) was added drop wise to 4-phenylamino-benzoic acid (preparation as described above) (75 mg, 0.35 mmol) in DMF (4 mL). EDCI (167 mg, 0.87 mmol) and HOBT (56 mg, 0.42 mmol) were added consecutively and, after 10 minutes, 2-amino-1-[4-(2,4-dichloro-benzoyl)-piperazin-1-yl]-ethanone in its TFA salt form (180 mg, 0.42 mmol) was added. The resulting mixture was stirred at room temperature overnight. Cold water was then added, filtered the solid precipitated. The solid was purified by column chromatography (using silica gel of 60-120 mesh and 70% EtOAc in Hexane as eluent) to afford 95 mg (53% yield) of N-{2-[4-(2,4-Dichloro-benzoyl)-piperazin-1-yl]-2-oxo-ethyl}-4-phenylamino-benzamide. LC-MS purity: 96.05%. 1H-NMR (DMSO-D6): δ 8.6 (s, 1H), 8.3 (t, 1H), 7.8 (d, 3H), 7.5 (m, 2H), 7.3 (t, 2H), 7.2 (d, 2H), 7.1 (d, 2H), 6.9 (t, 1H), 4.1 (dd, 2H), 3.6 (m, 4H), 3.5 (m, 2H), 3.2 (m, 2H).

후처리

  1. filtrationfiltered the solid
  2. customprecipitated
  3. customThe solid was purified by column chromatography (using silica gel of 60-120 mesh and 70% EtOAc in Hexane as eluent)

출처 및 근거

ORD 기록
ord-dec64cf49dae4c5da0fd509b9e141d30
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07842696B2

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