1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 5-phenyl-1H-pyrrole-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide

HRID 1178115노트

반응식

HRID 1178115 반응식
CCN(C(C)C)C(C)C.[C:10]1([C:16]2[NH:20][C:19]([C:21]([OH:23])=O)=[CH:18][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.[NH2:46][CH2:47][C:48]([N:50]1[CH2:55][CH2:54][N:53]([C:56](=[O:67])[C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=2[C:63]([F:66])([F:65])[F:64])[CH2:52][CH2:51]1)=[O:49]>CN(C=O)C.O>[O:49]=[C:48]([N:50]1[CH2:51][CH2:52][N:53]([C:56](=[O:67])[C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][C:58]=2[C:63]([F:66])([F:65])[F:64])[CH2:54][CH2:55]1)[CH2:47][NH:46][C:21]([C:19]1[NH:20][C:16]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:17][CH:18]=1)=[O:23]

참가 물질

8

반응물 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2261995-phenyl-1H-pyrrole-2-carboxylic acidHCID 669531782-Amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride

생성물 1

HCID 251655355-phenyl-1H-pyrrole-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide수율 72%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

DIPEA (102 mg, 0.14 mL, 0.79 mmol) was added to a stirred solution of 5-phenyl-1H-pyrrole-2-carboxylic acid (37 mg, 0.19 mmol) in DMF (4 mL). HOBT (30 mg, 0.22 mmol) and EDCI (57 mg, 0.29 mmol) were then added at room temperature. After 2 minutes, 2-amino-1-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethanone hydrochloride salt (prepared by the method as described above) (83.6 mg, 0.23 mmol) was added and the resulting mixture was stirred at room temperature overnight. Cold water was then added and filtered the solid precipitated to afford 69 mg (72% yield) of 5-phenyl-1H-pyrrole-2-carboxylic acid {2-oxo-2-[4-(2-trifluoromethyl-benzoyl)-piperazin-1-yl]-ethyl}-amide. LCMS Purity: 89.78%. 1H NMR (DMSO-d6): δ 11.7 (s, 1H), 8.2-8.1 (bs, 1H), 7.9-7.7 (s, 4H), 7.7-7.6 (s, 1H), 7.6-7.5 (s, 1H), 7.45-7.3 (t, 2H), 7.3-7.2 (t, 1H), 6.9-6.8 (s, 1H), 6.6-6.5 (s, 1H), 4.28-4.04 (d, 2H), 3.84-3.5 (bs, 4H), 3.5-3.4 (s, 2H), 3.2-3.0 (d, 2H).

후처리

  1. additionwas added
  2. filtrationfiltered the solid
  3. customprecipitated

출처 및 근거

ORD 기록
ord-bdd16a69a3814a41b81b453ed1895f56
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07842696B2

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